Insecticidal Compositions of 2-Cyanobenzene Sulfonamide Compounds and Isomeric Forms Thereof Having Improved Effect

ABSTRACT

The present invention comprises 2-cyanobenzenesulfonic acid amides of the formula (I) and isomeric forms thereof (I-A) and (I-B) 
     
       
         
         
             
             
         
       
         
         wherein 
         R 1 , R 2 , R 3 , R 4 , R 5  and A have the aforesaid meaning for the control of animal pests with the use of penetration enhancers and/or ammonium or phosphonium salts.

The invention relates to the improvement of the action of pesticides, in particular of 2-cyano-benzenesulfonamide compounds of the formula (I), isomeric forms thereof (I-A) and (I-B), in which the variables R¹ to R⁵ are defined as in claim 2, and/or agriculturally useful salts thereof through the addition of ammonium or phosphonium salts and optionally penetration enhancers, and the corresponding agents, processes for the production thereof and their use in plant protection, in particular as insecticides and/or acaricides. The present invention further relates to the use of compounds (I), (I-A) or (I-B) and/or salts thereof through the addition of ammonium or phosphonium salts for the control of animal pests, agricultural compositions, which contain a pesticidally effective quantity of at least one compound of the general formula I, (I-A) or (I-B) and/or of at least one agriculturally useful salt of I, (I-A) or (I-B) and of at least one inert liquid and/or solid agriculturally acceptable carrier and at least one penetration enhancer and/or ammonium or phosphonium salts, and a method for the control of animal pests, wherein the animal pests, their environment, their breeding grounds, their nutrition source, the plant, the seeds, the soil, the area, the substance or the environment in which the animal pests grow or can grow, or the substances, plants, seeds, soils, areas or spaces which are to be protected against infestation or contamination with the animals are treated with a pesticicidally effective quantity of at least one 2-cyanobenzenesulfonamide compound of the general formula (I), (I-A) or (I-B) and/or at least one agriculturally acceptable salt thereof.

Animal pests destroy standing and harvested crops and attack wooden buildings and structures, as a result of which they cause major economic losses in food production and to property. Although a large number of pesticidal agents are known, there is still a demand for new agents for the control of animal pests, since the pests to be controlled can develop resistance to these agents. In particular, animal pests such as insects and spider mites are difficult to control effectively.

EP 0033984 describes substituted 2-cyanobenzenesulfonamide compounds with aphicidal activity. The benzenesulfonamide compounds preferably bear a fluorine atom or chlorine atom in the 3 position of the phenyl ring. Also known in WO 2005/035486 and WO 2006/056433 were 2-cyano-benzenesulfonamides with insecticidal action. Their use for soil and seed applications is described in WO2006/100271 and WO 2006/100288. In addition, isomeric forms of the 2-cyanobenzene-sulfonamides and derivatives of the isomeric forms and their insecticidal action are also described in EP 86748, EP 110829, EP 133418, EP 138762, DE 3544436, EP 191734, EP 207891, JP 1989/319467 and JP 1990/006496. Further, 2-cyanobenzenesulfonamides are described in WO 2007/060220 and WO 2008/031712. Reference is hereby expressly made to these publications.

All the active substances contained in the agents according to the invention are already known and can be produced by processes described in the state of the art (see references cited above). Their pesticidal action is good, but not always completely satisfactory, particularly at low application doses and concentrations. There is therefore a need for an increase in the activity of the pesticides containing the compounds.

The target of the present invention are therefore agents and methods for the improvement of the activity of compounds of the general formula (I), (I-A) and (I-B), in particular against insects and spider mites, which are difficult to control.

In the literature, it has already been stated that the action of various active substances can be increased by addition of ammonium salts. However, these are salts with detergent action (e.g. WO 95/017817) or salts with longer alkyl and/or aryl substituents which have a permeabilizing action or increase the solubility of the active substance (e.g. EP-A 0 453 086, EP-A 0 664 081, FR-A 2 600 494, U.S. Pat. No. 4,844,734, U.S. Pat. No. 5,462,912, U.S. Pat. No. 5,538,937, U.S.-A 03/0224939, U.S.-A 05/0009880, U.S.-A 05/0096386). Further, the state of the art describes the action only for certain active substances and/or certain uses of the agents in question. In yet other cases, they are salts of sulfonic acids, with which the acids themselves have a paralyzing action on insects (U.S. Pat. No. 2,842,476). An increase in activity e.g. due to ammonium sulfate is for example described for the herbicides glyphosate and phosphinothricin (U.S. Pat. No. 6,645,914, EP-A2 0 036 106). A corresponding action with insecticides is neither disclosed nor rendered obvious by this state of the art.

The use of ammonium sulfate as a formulation additive is also described for certain active substances and uses (WO 92/16108), but there it serves for stabilization of the formulation, not for increasing the activity.

It has now entirely surprisingly been found that the action of insecticides and/or acaricides of the 2-cyanobenzenesulfonamide class (I) and isomeric forms thereof (I-A) and (I-B) can be markedly increased by the addition of ammonium or phosphonium salts to the application solution or through the incorporation of these salts into a formulation containing 2-cyanobenzenesulfonamides (I), and isomeric forms thereof (I-A) and (I-B). A subject of the present invention is thus the use of ammonium or phosphonium salts for increasing the action of pesticides that contain insecticidally and/or acarcidallly active 2-cyanobenzenesulfonamides (I) and isomeric forms thereof (I-A) and (I-B) as the active substance. Also a subject of the invention are agents which contain insecticidally active 2-cyanobenzenesulfonamides (I) and isomeric forms thereof (I-A) and (I-B) and ammonium or phosphonium salts increasing their action, namely both formulated active substances and also ready-for-use agents (sprays). Finally, a further subject of the invention is the use of these agents for the control of noxious insects and/or spider mites.

The 2-cyanobenzenesulfonamide compounds (I) and isomeric forms thereof (I-A) and (I-B) are described by the general formulae

-   in which -   A stands for hydrogen, C₁-C₆ alkyl or C₂-C₆ alkenyl -   R¹ stands for hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄     alkoxy or C₁-C₄ halo-alkoxy; -   R² stands for hydrogen, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl,     C₃-C₈ cycloalkyl or C₁-C₄ alkoxy, where the five last-named residues     can be unsubstituted, partly or completely halogenated and/or can     bear one, two or three residues from the group C₁-C₄ alkoxy, C₁-C₄     alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄     haloalkoxy, C₁-C₄ haloalkylthio, C₁-C₄ alkylcarbonyl, C₁-C₄     alkoxycarbonyl, cyano, amino, (C₁-C₄ alkyl)amino, di-(C₁-C₄     alkyl)amino, C₃-C₈ cycloalkyl and phenyl, wherein the phenyl can be     unsubstituted, partly or completely halogenated and/or can bear one,     two or three substituents from the group C₁-C₄ alkyl, C₁-C₄     haloalkyl, C₁-C₄ alkoxy or C₁-C_(a) haloalkoxy; -   R³, R⁴ and R⁵ mutually independently stand for hydrogen, halogen,     cyano, nitro, C₁-C₆ alkyl, C₃-C₈ cycloalkyl, C₁-C₄ haloalkyl, C₁-C₄     alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl,     C₁-C₄ haloalkoxy, C₁-C₄ haloalkylthio, C₂-C₆ alkenyl, C₂-C₆ alkynyl,     C₁-C₄ alkoxycarbonyl, amino, (C₁-C₄ alkyl)amino, di-(C₁-C₄     alkyl)amino, aminocarbonyl, (C₁-C₄ alkyl)aminocarbonyl and di-(C₁-C₄     alkyl)aminocarbonyl.

Here compounds of the formula (I) in which A stands for hydrogen can optionally be present in the isomeric form (I-A); compounds of the formula (I) in which A and R² stand for hydrogen can optionally be present in the isomeric form (I-B).

The compounds of the formula (I) and isomeric forms thereof (I-A) and (I-B) have a broad insecticidal and/or acaricidal action, but in specific cases the action leaves something to be desired.

The active substances can be used in the compositions according to the invention in a broad concentration range. However, the concentration of the active substances in the formulation is usually 0.1-50 wt. %.

Ammonium and phosphonium salts which according to the invention increase the action of pesticides containing 2-cyanobenzenesulfonamides and isomeric forms thereof (I-A) and (I-B) are defined by formula (II)

-   in which -   D stands for nitrogen or phosphorus, -   D preferably stands for nitrogen, -   R⁶, R⁷, R⁸ and R⁹ mutually independently stand for hydrogen or each     for optionally substituted C₁-C₈ alkyl or singly or multiply     unsaturated, optionally substituted C₁-C₈ alkylene, wherein the     substituents can be selected from halogen, nitro and cyano, -   R⁶, R⁷, R⁸ and R⁹ preferably mutually independently stand for     hydrogen or each stand for optionally substituted C₁-C₄ alkyl,     wherein the substituents can be selected from halogen, nitro and     cyano, -   R⁶, R⁷, R⁸ and R⁹ particularly preferably mutually independently     stand for hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl,     i-butyl, s-butyl or t-butyl, -   R⁶, R⁷, R⁸ and R⁹ quite especially preferably stand for hydrogen, -   n stands for 1, 2, 3 or 4, -   n preferably stands for 1 or 2, -   R¹⁰ stands for an inorganic or organic anion, -   R¹⁰ preferably stands for hydrogen carbonate, tetraborate, fluoride,     bromide, iodide chloride, monohydrogen phosphate, dihydrogen     phosphate, hydrogen sulfate, tartrate, sulfate, nitrate,     thiosulfate, thiocyanate, formate, lactate, acetate, propionate,     butyrate, pentanoate, citrate or oxalate, -   R¹⁰ particularly preferably stands for lactate, sulfate,     monohydrogen phosphate, dihydrogen phosphate, nitrate, thiosulfate,     thiocyanate, citrate, oxalate or formate.

R¹⁰ quite especially preferably stands for sulfate.

The ammonium and phosphonium salts of the formula (II) can be used over a broad concentration range for increasing the action of pesticides containing 2-cyanobenzenesulfonamides and/or isomeric forms thereof. In general, the ammonium or phosphonium salts are used in the ready-for-use pesticide at a concentration of 0.5 to 80 mmol/l, preferably 0.75 to 37.5 mmol/l, particularly preferably 1.5 to 25 mmol/l. In the case of a formulated product, the ammonium and/or phosphonium salt concentration in the formulation is selected so that after dilution of the formulation to the desired active substance concentration it lies in these stated general, preferred or particularly preferred ranges. The concentration of the salt in the formulation here is usually 1-50 wt. %.

In a preferred embodiment of the invention, not only an ammonium and/or phosphonium salt, but also in addition a penetration enhancer, is added to the pesticides to increase the activity. It must be described as entirely surprising that even in these cases a still further increase in activity is to be observed. Hence also a subject of the present invention is the use of a combination of penetration enhancers and ammonium and/or phosphonium salts for increasing the activity of pesticides which contain akaricidally/insecticidally active 2-cyanobenzenesulfonamides and/or isomeric forms thereof (I-A) and (I-B) as the active substance. Also a subject of the invention are agents which contain insecticidally active 2-cyanobenzenesulfonamides and/or isomeric forms thereof (I-A) and (I-B), penetration enhancers and ammonium and/or phosphonium salts, namely both formulated active substances and also ready-for-use agents (sprays). Finally, also a subject of the invention is the use of these agents for the control of noxious insects.

Possible penetration enhancers in the present connection are all those substances which are normally used in order to improve the penetration of agrochemical active substances in plants. In this connection, penetration enhancers are defined by the fact that they penetrate from the aqueous spray and/or the spray deposit into the cuticle of the plant and thereby are able to increase the mobility of active substances in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used for the determination of this property.

Possible penetration enhancers are for example alkanol alkoxylates. Penetration enhancers according to the invention are alkanol alkoxylates of the formula

R—O-(-AO)_(v-)R′  (III)

-   in which -   R stands for linear or branched alkyl with 4 to 20 carbon atoms, -   R′ stands for hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl,     i-butyl, t-butyl, n-pentyl or n-hexyl, -   AO stands for an ethylene oxide residue, a propylene oxide residue,     a butylene oxide residue or for mixtures of ethylene oxide and     propylene oxide residues or butylene oxide residues and -   v stands for numbers from 2 to 30.

A preferred group of penetration enhancers are alkanol alkoxylates of the formula

R—O-(-EO—)_(n)—R′  (III-a)

-   in which -   R has the aforesaid meaning, -   R′ has the aforesaid meaning, -   EO stands for —CH₂—C₂—O— and -   n stands for numbers from 2 to 20.

A further preferred group of penetration enhancers are alkanol alkoxylates of the formula

R—O-(-EO—)_(p)—(—PO—)_(q)—R′  (III-b)

-   in which -   R has the aforesaid meaning, -   R′ has the aforesaid meaning, -   EO stands for —CH₂—CH₂—O—, -   PO stands for

-   p stands for numbers from 1 to 10 and -   q stands for numbers from 1 to 10.

A further preferred group of penetration enhancers are alkanol alkoxylates of the formula

R—O—(—PO-)_(r)-(EO—)_(s)—R′  (III-c)

-   in which -   R has the aforesaid meaning, -   R′ has the aforesaid meaning, -   EO stands for —CH₂—CH₂—O—, -   PO stands for

-   r stands for numbers from 1 to 10 and -   s stands for numbers from 1 to 10.

A further preferred group of penetration enhancers are alkanol alkoxylates of the formula

R—O-(-EO—)_(p)—(—BO—)_(q)—R′  (III-d)

-   in which -   R and R′ have the aforesaid meanings, -   EO stands for CH₂—CH₂—O—, -   BO stands for

-   p stands for numbers from 1 to 10 and -   q stands for numbers from 1 to 10.

A further preferred group of penetration enhancers are alkanol alkoxylates of the formula

R—O—(—BO-)_(r)-(-EO—)_(s)—R′  (III-e)

-   in which -   R and R′ have the aforesaid meanings, -   BO stands for

-   EO stands for CH₂—CH₂—O—, -   r stands for numbers from 1 to 10 and -   s stands for numbers from 1 to 10.

A further preferred group of penetration enhancers are alkanol alkoxylates of the formula

CH₃—(CH₂)_(t)—CH₂—O—(—CH₂—CH₂—O—)_(u)—R′  (III-f)

-   in which -   R′ has the aforesaid meaning, -   t stands for numbers from 8 to 13 and -   u stands for numbers from 6 to 17.

In the aforesaid formulae

-   R preferably stands for butyl, i-butyl, n-pentyl, i-pentyl,     neopentyl, n-hexyl, i-hexyl, n-octyl, i-octyl, 2-ethylhexyl, nonyl,     i-nonyl, decyl, n-dodecyl, i-dodecyl, lauryl, myristyl, i-tridecyl,     trimethyl-nonyl, palmityl, stearyl or eicosyl.

As an example of an alkanol alkoxylate of the formula (III-c), 2-ethylhexyl alkoxylate of the formula

-   in which -   EO stands for —CH₂—CH₂—O—, -   PO stands for

-   and -   the numbers 8 and 6 are average values may be mentioned.

As an example of an alkanol alkoxylate of the formula (III-d), the formula

CH₃—(CH₂)₁₀—O-(-EO—)₆—(—BO—)₂—CH₃  (III-d-1)

-   in which -   BO stands for CH₂—CH₂—O—, -   BO stands for

-   and -   the numbers 10, 6 and 2 are average values, may be mentioned.

Particularly preferable alkanol alkoxylates of the formula (III-f) are compounds of this formula, in which

-   t stands for numbers from 9 to 12 and -   u for numbers from 7 to 9.

Quite especially preferably, alkanol alkoxylate of the formula (III-f-1)

CH₃—(CH₂)_(t)—CH₂—O—(—CH₂—CH₂—O—)_(u)—R′  (III-f-1)

-   in which -   t stands for the average value 10.5 and -   u stands for the average value 8.4 may be mentioned.

The alkanol alkoxylates are generally defined by the above formulae. These substances are mixtures of substances of the stated type with different chain lengths. Average values, which can also deviate from whole numbers, are therefore calculated for the indices.

The alkanol alkoxylates of the stated formulae are known and some are commercially available or can be produced by known methods (see. WO 98/35 553, WO 00/35 278 and EP-A 0 681 865).

Also possible as penetration enhancers are for example substances which promote the solubility of the compounds of the formula (I) in the spray deposit. These for example include mineral or vegetable oils. Possible oils are all mineral or vegetable—optionally modified—oils normally usable in agrochemical agents. By way of example, sunflower oil, rape oil, olive oil, castor oil, turnip oil, corn seed oil, cottonseed oil and soybean oil or the esters of said oils may be mentioned. Rape oil, sunflower oil and the methyl or ethyl esters thereof are preferred.

The concentration of penetration enhancers in the agents according to the invention can be varied over a wide range. In a formulated pesticide, it is generally about 1 to 95 wt. %, preferably about 1 to 55 wt. %, particularly preferably about 15-40 wt. %. In the ready-to-use agents (sprays), the concentrations generally lie between 0.1 and 10 g/l, preferably between 0.5 and 5 g/l.

Combinations of active substance, salt and penetration enhancer emphasized according to the invention are set out in the following table. Here “as per test” means that any compound which acts as a penetration enhancer in the test for cuticle penetration (Baur et al., 1997, Pesticide Science 51, 131-152) is suitable.

TABLE 1 Active Penetration No. substance Salt enhancer 1 I, IA, IB Ammonium sulfate as per test 2 I, IA, IB Ammonium lactate as per test 3 I, IA, IB Ammonium nitrate as per test 4 I, IA, IB Ammonium thiosulfate as per test 5 I, IA, IB Ammonium thiocyanate as per test 6 I, IA, IB Ammonium citrate as per test 7 I, IA, IB Ammonium oxalate as per test 8 I, IA, IB Ammonium formate as per test 9 I, IA, IB Ammonium hydrogen phosphate as per test 10 I, IA, IB Ammonium dihydrogen phosphate as per test 11 I, IA, IB Ammonium carbonate as per test 12 I, IA, IB Ammonium benzoate as per test 13 I, IA, IB Ammonium sulfite as per test 14 I, IA, IB Ammonium benzoate as per test 15 I, IA, IB Ammonium hydrogen oxalate as per test 16 I, IA, IB Ammonium hydrogen citrate as per test 17 I, IA, IB Ammonium acetate as per test 18 I, IA, IB Tetramethylammonium sulfate as per test 19 I, IA, IB Tetramethylammonium lactate as per test 20 I, IA, IB Tetramethylammonium nitrate as per test 21 I, IA, IB Tetramethylammonium thiosulfate as per test 22 I, IA, IB Tetramethylammonium thiocyanate as per test 23 I, IA, IB Tetramethylammonium citrate as per test 24 I, IA, IB Tetramethylammonium oxalate as per test 25 I, IA, IB Tetramethylammonium formate as per test 26 I, IA, IB Tetramethylammonium hydrogen as per test phosphate 27 I, IA, IB Tetramethylammonium dihydrogen as per test phosphate 28 I, IA, IB Tetraethylammonium sulfate as per test 29 I, IA, IB Tetraethylammonium lactate as per test 30 I, IA, IB Tetraethylammonium nitrate as per test 31 I, IA, IB Tetraethylammonium thiosulfate as per test 32 I, IA, IB Tetraethylammonium thiocyanate as per test 33 I, IA, IB Tetraethylammonium citrate as per test 34 I, IA, IB Tetraethylammonium oxalate as per test 35 I, IA, IB Tetraethylammonium formate as per test 36 I, IA, IB Tetraethylammonium hydrogen as per test phosphate 37 I, IA, IB Tetraethylammonium dihydrogen as per test phosphate

Pesticides according to the invention can also contain other components, for example surfactants or dispersion aids or emulsifiers.

As nonionic surfactants or dispersion aids, all substances of this type normally usable in agro-chemical agents are possible. Preferably, polyethylene oxide polypropylene oxide block copolymers, polyethylene glycol ethers of linear alcohols, reaction products of fatty acids with ethylene oxide and/or propylene oxide, and also polyvinyl alcohol, polyvinylpyrrolidone, mixed polymerization products from polyvinyl alcohol and polyvinylpyrrolidone and copolymers of (meth)acrylic acid and (meth)acrylate esters, and also alkyl ethoxylates and alkylaryl ethoxylates, which can optionally be phosphated and optionally be neutralized with bases, may be mentioned, sorbitol ethoxylates being mentioned by way of example, and polyoxyalkylenamine derivatives.

As anionic surfactants, all substances of this type normally usable in agrochemical agents are possible. Alkali metal and alkaline earth metal salts of alkylsulfonic acids or alkylarylsulfonic acids are preferred.

A further preferred group of anionic surfactants or dispersion aids are poorly soluble in plant oil salts of polystyrenesulfonic acids, salts of polyvinylsulfonic acids, salts of naphthalenesulfonic acid-formaldehyde condensation products, salts of condensation products from naphthalenesulfonic acid, phenolsulfonic acid and formaldehyde and salts of ligninsulfonic acid.

Possible additives which can be contained in the formulations according to the invention are emulsifiers, foam suppressants, preservatives, antioxidants, colorants and inert fillers.

Preferred emulsifiers are ethoxylated alkylphenols, reaction products of alkylphenols with ethylene oxide and/or propylene oxide, ethoxylated arylalkylphenols, and also ethoxylated and propoxylated arylalkylphenols, and sulfated or phosphated arylalkyl ethoxylates or ethoxy-propoxylates, and sorbitan derivatives such as polyethylene oxide-sorbitan fatty acid esters and sorbitan fatty acid esters may be mentioned by way of example.

The following examples serve to illustrate the invention and should in no way be interpreted as limiting.

The compounds of the general formula (I) and (I-A) can have one or more chiral centers in the substituents A, R¹ to R⁵, and are then present as mixtures of enantiomers or diastereomers. The present invention provides both the pure enantiomers or diastereomers and also mixtures thereof.

Salts of the compounds of the formula (I), (I-A) or (I-B) which are suitable for the use according to the invention are in particular agriculturally acceptable salts. These can be formed in standard ways, e.g. by reacting the compound with an acid of the anion in question.

Suitable agriculturally useful salts are in particular the salts of those cations or the acid addition salts of those acids, the cations or anions whereof have no adverse effects on the action of the compounds according to the invention which are suitable for the control of noxious insects or arachnids. Suitable cations are thus in particular the ions of the alkali metals, preferably lithium, sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, which can if desired bear one to four C₁-C₄ alkyl substituents and/or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium or trimethyl-benzylammonium, or also phosphonium ions, sulfonium ions, preferably tri(C₁-C₄ alkyl)sulfonium and sulfoxonium ions, preferably tri(C₁-C₄ alkyl)sulfoxonium.

Anions of useful acid addition salts are first and foremost chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of the C₁-C₄ alkanoic acids, preferably formate, acetate, propionate and butyrate. These can be formed by reacting the compounds of the formulae Ia and Ib with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

The organic residues mentioned in the aforesaid definitions of the variables, like the term halogen, are collective terms for particular enumerations of particular group members. The prefix “C_(n)-C_(m)” in each states the possible number of carbon atoms in the group.

In each case, the term halogen means fluorine, bromine, chlorine or iodine.

Examples of further meanings are:

In the present connection, the term “C₁-C₄ alkyl” and the alkyl residues of alkylamino and dialkylamino mean a saturated linear or branched hydrocarbon residue with 1 to 4 carbon atoms, i.e. for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl.

In the present connection, the term “C₁-C₆ alkyl” means a saturated linear or branched hydrocarbon residue with 1 to 6 carbon atoms, i.e. for example one of the residues which were mentioned under C₁-C₄ alkyl, and n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl.

In the present connection, the term “C₁-C₄ haloalkyl” means a linear or saturated alkyl residue with 1 to 4 carbon atoms (as aforesaid), wherein some or all of the hydrogen atoms in these residues can be replaced by fluorine, chorine, bromine and/or iodine, i.e. for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloro-fluoromethyl, dichlorofluoromethyl, chlordifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromo-ethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl.

In the present connection, the term “C₁-C₂ fluoroalkyl” means a C₁-C₂ alkyl residue which bears 1, 2, 3, 4 or 5 fluorine atoms, for example difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoro-ethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl or pentafluoroethyl.

In the present connection, the term “C₁-C₄ alkoxy” means a linear or branched saturated alkyl residue with 1 to 4 carbon atoms (as aforesaid), which is linked via an oxygen atom, i.e. for example methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methyl-propoxy or 1,1-dimethylethoxy.

In the present connection, the term “C₁-C₄ haloalkoxy” means a C₁-C₄ alkoxy residue as aforesaid, which is partly or wholly substituted with fluorine, chlorine, bromine and/or iodine, i.e. for example chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoro-ethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloro-ethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoro-propoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromo-propoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, hepta-fluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromo-methyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.

In the present connection, the term “C₁-C₄ alkylthio(C₁-C₄ alkylsulfanyl: C₁-C₄ alkyl-S—)” means a linear or branched saturated alkyl residue with 1 to 4 carbon atoms (as aforesaid), which is linked via a sulfur atom, i.e. for example methylthio, ethylthio, n-propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio.

In the present connection, the term “C₁-C₄ alkylsulfinyl” (C₁-C₄ alkyl-S(═O)—) means a linear or branched saturated hydrocarbon residue with 1 to 4 carbon atoms (as aforesaid), which is linked via the sulfur atom of the sulfinyl group to any bond in the alkyl residue, i.e. for example SO—CH₃, SO—C₂H₅, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethyl]ethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropyl-sulfinyl, 2,2-dimethylpropylsulfinyl or 1-ethylpropylsulfinyl.

In the present connection, the term “C₁-C₄ alkylsulfonyl” (C₁-C₄ alkyl-S(═O)₂—) means a linear or branched saturated alkyl residue with 1 to 4 carbon atoms (as aforesaid), which is linked via the sulfur atom of the sulfonyl group to any bond in the alkyl residue, i.e. for example SO₂—CH₃, SO₂—C₂H₅, n-propylsulfonyl, SO₂—CH(CH₃)₂, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl or SO₂—C(CH₃)₃.

In the present connection, the term “C₁-C₄ haloalkylthio” means a C₁-C₄ alkylthio residue as aforesaid, which is partly or wholly substituted with fluorine, chlorine, bromine and/or iodine, i.e. for example fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoro-propylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoro-propylthio, 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio, 1-(bromo-methyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluoro-butylthio.

In the present connection, the term “C₁-C₄ alkoxycarbonyl” means a linear or branched saturated alkoxy residue with 1 to 4 carbon atoms (as aforesaid), which is linked via the carbon atom of the carbonyl group, i.e. for example methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methyl-ethoxycarbonyl, n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1,1-dimethylethoxycarbonyl.

In the present connection, the term “C₁-C₄ alkylcarbonyl” means a linear or branched saturated alkyl residue with 1 to 4 carbon atoms (as aforesaid), which is linked via the carbon atom of the carbonyl group, i.e. for example methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, 1-methylethyl-carbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1,1-dimethylethyl-carbonyl.

In the present connection, the term “(C₁-C₄ alkylamino)carbonyl” for example means methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, butylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or 1,1-dimethylethylaminocarbonyl.

In the present connection, the term “Di-(C₁-C₄ alkyl)aminocarbonyl” for example means N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, N,N-di-(1-methylethyl)aminocarbonyl, N,N-dipropylaminocarbonyl, N,N-butylaminocarbonyl, N,N-di-(1-methylpropyl)aminocarbonyl, N,N-di(2-methylpropyl)aminocarbonyl, N,N-di-(1,1-dimethylethyl)aminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl-N-(1-methylethyl)amino-carbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N-(1-methylpropyl)aminocarbonyl, N-methyl-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-ethyl-aminocarbonyl, N-ethyl-N-(1-methylpropyl)aminocarbonyl, N-ethyl-N-(2-methylpropyl)amino-carbonyl, N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylethyl)-N-propylamino-carbonyl, N-butyl-N-propylaminocarbonyl, N-(1-methylpropyl)-N-propylaminocarbonyl, N-(2-methylpropyl)-N-propylaminocarbonyl, N-(1,1-dimethylethyl)-N-propylaminocarbonyl, N-butyl-N-(1-methylethyl)aminocarbonyl, N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl, N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)-aminocarbonyl, N-butyl-N-(1-methylpropyl)aminocarbonyl, N-butyl-N-(2-methylpropyl)amino-carbonyl, N-butyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylpropyl)-N-(2-methylpropyl)-aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl or N-(1,1-dimethyl-ethyl)-N-(2-methylpropyl)aminocarbonyl.

In the present connection, the term “C₂-C₆ alkenyl” means a linear or branched singly unsaturated hydrocarbon residue with 2 to 6 carbon atoms and a double bond in any position, i.e. for example ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl.

In the present connection, the term “C₂-C₆ alkynyl” means a linear or branched aliphatic hydrocarbon residue which contains a C—C triple bond and has 2 to 6 carbon atoms: for example ethynyl, prop-1-yn-1-yl, prop-2-yn-1-yl, n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl, n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl, n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl and the like.

In the present connection, the term “C₃-C₈ cycloalkyl” means a mononuclear hydrocarbon residue with 3 to 8 carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.

Among the 2-cyanobenzenesulfonamide compounds of the general formula (I), (I-A) and (I-B), those are preferred wherein the variables A, R¹ and R² mutually independently, but in particular in combination, have the meanings set out below:

-   A means hydrogen, C₁-C₄ alkyl, in particular methyl or ethyl -   R¹ means hydrogen, fluorine, chlorine, bromine, C₁-C₂ alkyl, in     particular methyl, trifluoromethyl or C₁-C₂ alkoxy, in particular     methoxy; -   R² means hydrogen or a linear, cyclic or branched chain hydrocarbon     residue with 1 to 4 carbon atoms, e.g. C₁-C₄ alkyl, in particular     methyl, ethyl, n-propyl, 1-methylethyl, cyclopropyl, C₁-C₄     alkoxy-C₁-C₄ alkyl, in particular 2-methoxyethyl, C₁-C₄     alkylthio-C₁-C₄ alkyl, in particular 2-methylthioethyl or C₂-C₄     alkynyl, in particular prop-2-yn-1-yl (propargyl). Most strongly     preferred are compounds I in which A stands for hydrogen and R² is     from the range methyl, ethyl, 1-methylethyl and prop-2-yn-1-yl.

Also preferred are those 2-cyanobenzenesulfonamide compounds of the general formula (I), (I-A) and (I-B) in which R¹ means C₁-C₄ haloalkoxy, especially C₁ haloalkoxy, in particular trifluoromethoxy, difluoromethoxy or chlorodifluoromethoxy. In these compounds, A has the aforesaid meanings, preferably hydrogen, methyl or ethyl and R² the aforesaid meanings, preferably hydrogen or a linear, cyclic or branched chain hydrocarbon residue with 1 to 4 carbon atoms, e.g. C₁-C₄ alkyl, especially methyl, ethyl, n-propyl, 1-methylethyl, cyclopropyl, C₁-C₄ alkoxy-C₁-C₄ alkyl, especially 2-methoxyethyl, C₁-C₄ alkylthio-C₁-C₄ alkyl, especially 2-methyl-thioethyl or C₂-C₄ alkynyl, especially prop-2-yn-1-yl (propargyl). Most strongly preferred are compounds of the formula (I) and (I-A), in which A for hydrogen and R² is from the range methyl, ethyl, 1-methylethyl and prop-2-yn-1-yl.

A preferred embodiment of the present invention relates to 2-cyanobenzenesulfonamide compounds of the general formula (I), (I-A) and (I-B) in which the variables A, R¹ and R² have the aforesaid meanings, in particular those meanings which are cited as preferred, and at least one of the residues R³, R⁴ or R⁵ differs from hydrogen, and preferably one or two of the residues R³, R⁴ or R⁵ mean hydrogen. Among these compounds, those compounds are preferred in which R³ differs from hydrogen and preferably means halogen, in particular chlorine or fluorine, and the other residues R⁴ and R⁵ mean hydrogen.

A further preferred embodiment of the present invention relates to 2-cyanobenzenesulfonamide compounds of the general formula (I), (I-A) and (I-B), in which the variables A, R¹ and R² have the aforesaid meanings, in particular those meanings which are cited as preferred, and each of the residues R³, R⁴ and R⁵ means hydrogen.

Examples of preferred compounds according to the invention of the formula (I),

which can optionally be present in their isomeric formulae (I-A) and (I-B), include those compounds which are cited in the following tables A1 to A16, wherein A, R³, R⁴, R⁵ are as defined in the tables, and R¹ and R² are cited in the rows of table A:

-   Table A1: compounds of the formula I wherein each of the residues A,     R³, R⁴ and R⁵ means hydrogen and R¹ and R² are as defined in a row     in table A. -   Table A2: compounds of the formula I wherein R³ means chlorine, A,     R⁴ and R⁵ mean hydrogen and R¹ and R² are as defined in a row in     table A. -   Table A3: compounds of the formula I wherein R³ means fluorine, A,     R⁴ and R⁵ mean hydrogen and R¹ and R² are as defined in a row in     table A. -   Table A4: compounds of the formula I wherein R³ means bromine, A, R⁴     and R⁵ mean hydrogen and R¹ and R² are as defined in a row in table     A. -   Table A5: compounds of the formula I wherein R³ means iodine, A, R⁴     and R⁵ mean hydrogen and R¹ and R² are as defined in a row in table     A. -   Table A6: compounds of the formula I wherein R³ means CH₃, A, R⁴ and     R⁵ mean hydrogen and R¹ and R² are as defined in a row in table A. -   Table A7: compounds of the formula I wherein R⁴ means chlorine, A,     R³ and R⁵ mean hydrogen and R¹ and R² are as defined in a row in     table A. -   Table A8: compounds of the formula I wherein R⁴ means fluorine, A,     R³ and R⁵ mean hydrogen and R¹ and R² are as defined in a row in     table A. -   Table A9: compounds of the formula I wherein R⁴ means bromine, A, R³     and R⁵ mean hydrogen and R¹ and R² are as defined in a row in table     A. -   Table A10: compounds of the formula I wherein R⁴ means iodine, A, R³     and R⁵ mean hydrogen and R¹ and R² are as defined in a row in table     A. -   Table A11: compounds of the formula I wherein R⁴ means CH₃, A, R³     and R⁵ mean hydrogen and R¹ and R² are as defined in a row in table     A. -   Table A12: compounds of the formula I wherein R⁵ means chlorine, A,     R³ and R⁴ mean hydrogen and R¹ and R² are as defined in a row in     table A. -   Table A13: compounds of the formula I wherein R⁵ means fluorine, A,     R³ and R⁴ mean hydrogen and R¹ and R² are as defined in a row in     table A. -   Table A14: compounds of the formula I wherein R⁵ means bromine, A,     R³ and R⁴ mean hydrogen and R¹ and R² are as defined in a row in     table A. -   Table A15: compounds of the formula I wherein R⁵ means iodine, A, R³     and R⁴ mean hydrogen and R¹ and R² are as defined in a row in table     A.

Table A16: compounds of the formula I wherein R⁵ means CH₃, A, R³ and R⁴ mean hydrogen and R¹ and R² are as defined in a row in table A.

TABLE A R¹ R² 1. CH₃ H 2. CH₃ CH₃ 3. CH₃ CH₃CH₂— 4. CH₃ (CH₃)₂CH— 5. CH₃ CH₃CH₂CH₂— 6. CH₃ n-C₄H₉ 7. CH₃ (CH₃)₃C— 8. CH₃ (CH₃)₂CHCH₂— 9. CH₃ n-C₅H₁₁ 10. CH₃ (CH₃)₂CH—CH₂—CH₂— 11. CH₃ (C₂H₅)₂—CH— 12. CH₃ (CH₃)₃C—CH₂— 13. CH₃ (CH₃)₃C—CH₂—CH₂— 14. CH₃ C₂H₅CH(CH₃)—CH₂— 15. CH₃ CH₃—CH₂ ^(—)C(CH₃)₂— 16. CH₃ (CH₃)₂CH—CH(CH₃)— 17. CH₃ (CH₃)₃C—CH(CH₃)— 18. CH₃ (CH₃)₂CH—CH₂—CH(CH₃)— 19. CH₃ CH₃—CH₂—C(CH₃)(C₂H₅)— 20. CH₃ CH₃—CH₂—CH₂—C(CH₃)₂— 21. CH₃ C₂H₅—CH₂—CH(CH₃)—CH₂— 22. CH₃ cyclopropyl 23. CH₃ cyclopropyl-CH₂— 24. CH₃ cyclopropyl-CH(CH₃)— 25. CH₃ cyclobutyl 26. CH₃ cyclopentyl 27. CH₃ cyclohexyl 28. CH₃ HC≡C—CH₂— 29. CH₃ HC≡C—CH(CH₃)— 30. CH₃ HC≡C—C(CH₃)₂— 31. CH₃ HC≡C—C(CH₃)(C₂H₅)— 32. CH₃ HC≡C—C(CH₃)(C₃H₇)— 33. CH₃ CH₂═CH—CH₂— 34. CH₃ H₂C═CH—CH(CH₃)— 35. CH₃ H₂C═CH—C(CH₃)₂— 36. CH₃ H₂C═CH—C(C₂H₅)(CH₃)— 37. CH₃ C₆H₅—CH₂— 38. CH₃ 4-(CH₃)₃C—C₆H₄—CH₂— 39. CH₃ C₆H₅—CH₂— 40. CH₃ 4-(CH₃)₃C—C₆H₄—CH₂— 41. CH₃ 4-Cl—C₆H₄—CH₂— 42. CH₃ 3-(CH₃O)—C₆H₄—CH₂— 43. CH₃ 4-(CH₃O)—C₆H₄—CH₂— 44. CH₃ 2-(CH₃O)—C₆H₄—CH₂— 45. CH₃ 3-Cl—C₆H₄—CH₂— 46. CH₃ 2-Cl—C₆H₄—CH₂— 47. CH₃ 4-(F₃C)—C₆H₄—CH₂— 48. CH₃ NC—CH₂— 49. CH₃ NC—CH₂—CH₂— 50. CH₃ NC—CH₂CH(CH₃)— 51. CH₃ NC—CH₂C(CH₃)₂— 52. CH₃ NC—CH₂—CH₂—CH₂— 53. CH₃ FH₂C—CH₂— 54. CH₃ ClH₂C—CH₂— 55. CH₃ BrH₂C—CH₂— 56. CH₃ FH₂C—CH(CH₃)— 57. CH₃ ClH₂C—CH(CH₃)— 58. CH₃ BrH₂C—CH(CH₃)— 59. CH₃ F₂HC^(—)CH₂— 60. CH₃ F₃C—CH₂— 61. CH₃ FH₂C—CH₂—CH₂— 62. CH₃ ClH₂C—CH₂—CH₂— 63. CH₃ BrH₂C—CH₂—CH₂— 64. CH₃ F₂HC—CH₂—CH₂— 65. CH₃ F₃C—CH₂—CH₂— 66. CH₃ CH₃—O—CH₂—CH₂— 67. CH₃ CH₃—S—CH₂—CH₂— 68. CH₃ CH₃—SO₂—CH₂—CH₂— 69. CH₃ C₂H₅—O—CH₂—CH₂— 70. CH₃ (CH₃)₂CH—O—CH₂—CH₂— 71. CH₃ C₂H₅—S—CH₂—CH₂— 72. CH₃ C₂H₅—SO₂—CH₂—CH₂ ^(—) 73. CH₃ (CH₃)₂N—CH₂—CH₂— 74. CH₃ (C₂H₅)₂N—CH₂—CH₂— 75. CH₃ [(CH₃)₂CH]₂N—CH₂—CH₂— 76. CH₃ CH₃—O—CH₂—CH(CH₃)— 77. CH₃ CH₃—S—CH₂—CH(CH₃)— 78. CH₃ CH₃—SO₂—CH₂—CH(CH₃)— 79. CH₃ C₂H₅—O—CH₂—CH(CH₃)— 80. CH₃ C₂H₅—S—CH₂—CH(CH₃)— 81. CH₃ C₂H₅—SO₂—CH₂—CH(CH₃)— 82. CH₃ (CH₃)₂N—CH₂—CH(CH₃)— 83. CH₃ (C₂H₅)₂N—CH₂—CH{CH₃)— 84. CH₃ [(CH₃)₂CH]₂N—CH₂—CH(CH₃)— 85. CH₃ CH₃—O—CH(CH₃)—CH₂— 86. CH₃ CH₃—S—CH(CH₃)—CH₂— 87. CH₃ CH₃—SO₂—CH(CH₃)—CH₂— 88. CH₃ C₂H₅—O—CH(CH₃)—CH₂— 89. CH₃ C₂H₅—S—CH(CH₃)—CH₂— 90. CH₃ C₂H₅—SO₂—CH(CH₃)—CH₂— 91. CH₃ (CH₃)₂N—CH(CH₃)—CH₂— 92. CH₃ (C₂H₅)₂N—CH(CH₃)—CH₂— 93. CH₃ [(CH₃)₂CH]₂N—CH(CH₃)—CH₂— 94. CH₃ CH₃—O—CH₂—CH₂—CH₂— 95. CH₃ CH₃—S—CH₂—CH₂—CH₂— 96. CH₃ CH₃—SO₂—CH₂—CH₂—CH₂— 97. CH₃ C₂H₅—O—CH₂—CH₂—CH₂— 98. CH₃ C₂H₅—S—CH₂—CH₂—CH₂— 99. CH₃ C₂H₅—SO₂—CH₂—CH₂—CH₂— 100. CH₃ (CH₃)₂N—CH₂—CH₂CH₂— 101. CH₃ (C₂H₅)₂N—CH₂—CH₂—CH₂— 102. CH₃ CH₃—O—CH₂—C(CH₃)₂— 103. CH₃ CH₃—S—CH₂—C(CH₃)₂— 104. CH₃ CH₃—SO₂—CH₂—C(CH₃)₂— 105. CH₃ C₂H₅—O—CH₂—C(CH₃)₂— 106. CH₃ C₂H₅—S—CH₂—C(CH₃)₂— 107. CH₃ C₂H₅—SO₂—CH₂—C(CH₃)₂— 108. CH₃ (CH₃)₂N—CH₂—C(CH₃)₂— 109. CH₃ (C₂H₅)₂N—CH₂—C(CH₃)₂— 110. CH₃ [(CH₃)₂CH]₂N—CH₂—C(CH₃)₂— 111. CH₃ Cl—CH₂—C≡C—CH₂— 112. CH₃ CH₃—O—C(O)—CH₂— 113. CH₃ C₂H₅—O—C(O)—CH₂— 114. CH₃ CH₃—O—C(O)—CH(CH₃)— 115. CH₃ C₂H₅—O—C(O)—CH(CH₃)— 116. CH₃ (CH₃O)₂CH—CH₂— 117. CH₃ (C₂H₅O)₂—CH—CH₂— 118. C₂H₅ H 119. C₂H₅ CH₃ 120. C₂H₅ CH₃CH₂— 121. C₂H₅ (CH₃)₂CH— 122. C₂H₅ CH₃CH₂CH₂— 123. C₂H₅ n-C₄H₉ 124. C₂H₅ (CH₃)₃C— 125. C₂H₅ (CH₃)₂CH—CH₂— 126. C₂H₅ n-C₅H₁₁ 127. C₂H₅ (CH₃)₂CH—CH₂CH₂— 128. C₂H₅ (C₂H₅)₂—CH— 129. C₂H₅ (CH₃)₃C—CH₂— 130. C₂H₅ (CH₃)₃C—CH₂—CH₂— 131. C₂H₅ C₂H₅—CH(CH₃)—CH₂— 132. C₂H₅ CH₃—CH₂—C(CH₃)₂— 133. C₂H₅ (CH₃)₂CH—CH(CH₃)— 134. C₂H₅ (CH₃)₃C—CH(CH₃)— 135. C₂H₅ (CH₃)₂CH—CH₂—CH(CH₃)— 136. C₂H₅ CH₃—CH₂—C(CH₃)(C₂H₅)— 137. C₂H₅ CH₃—CH₂—CH₂—C(CH₃)₂— 138. C₂H₅ C₂H₅—CH₂—CH(CH₃)—CH₂— 139. C₂H₅ cyclopropyl 140. C₂H₅ cyclopropyl-CH₂— 141. C₂H₅ cyclopropyl-CH(CH₃)— 142. C₂H₅ cyclobutyl 143. C₂H₅ cyclopentyl 144. C₂H₅ cyclohexyl 145. C₂H₅ HC≡C—CH₂— 146. C₂H₅ HC≡C—CH(CH₃)— 147. C₂H₅ HC≡C—C(CH₃)₂— 148. C₂H₅ HC≡C—C(CH₃)(C₂H₅)— 149. C₂H₅ HC≡C—C(CH₃)(C₃H₇)— 150. C₂H₅ CH₂═CH—CH₂— 151. C₂H₅ H₂C═CH—CH(CH₃)— 152. C₂H₅ H₂C═CH—C(CH₃)₂— 153. C₂H₅ H₂C═CH—C(C₂H₅)(CH₃)— 154. C₂H₅ C₆H₅—CH₂— 155. C₂H₅ 4-(CH₃)₃C—C₆H₄—CH₂— 156. C₂H₅ C₆H₅—CH₂— 157. C₂H₅ 4-(CH₃)₃C—C₆H₄—CH₂— 158. C₂H₅ 4-Cl—C₆H₄—CH₂— 159. C₂H₅ 3-(CH₃O)—C₆H₄—CH₂— 160. C₂H₅ 4-(CH₃O)—C₆H₄—CH₂— 161. C₂H₅ 2-(CH₃O)—C₆H₄—CH₂— 162. C₂H₅ 3-Cl—C₆H₄—CH₂— 163. C₂H₅ 2-Cl—C₆H₄—CH₂— 164. C₂H₅ 4-(F₃C)—C₆H₄—CH₂— 165. C₂H₅ NC—CH₂— 166. C₂H₅ NC—CH₂—CH₂— 167. C₂H₅ NC—CH₂—CH(CH₃)— 168. C₂H₅ NC—CH₂—C(CH₃)₂— 169. C₂H₅ NC—CH₂—CH₂—CH₂— 170. C₂H₅ FH₂C—CH₂— 171. C₂H₅ CIH₂C—CH₂— 172. C₂H₅ BrH₂C—CH₂— 173. C₂H₅ FH₂C—CH(CH₃)— 174. C₂H₅ CIH₂C—CH(CH₃)— 175. C₂H₅ BrH₂C—CH(CH₃)— 176. C₂H₅ F₂HC—CH₂— 177. C₂H₅ F₃C—CH₂— 178. C₂H₅ FH₂C—CH₂—CH₂— 179. C₂H₅ CIH₂C—CH₂—CH₂— 180. C₂H₅ BrH₂C—CH₂—CH₂— 181. C₂H₅ F₂HC—CH₂—CH₂— 182. C₂H₅ F₃C—CH₂—CH₂— 183. C₂H₅ CH₃—O—CH₂—CH₂— 184. C₂H₅ CH₃—S—CH₂—CH₂— 185. C₂H₅ CH₃—SO₂—CH₂—CH₂— 186. C₂H₅ C₂H₅—O—CH₂—CH₂— 187. C₂H_(S) (CH₃)₂CH—O—CH₂—CH₂— 188. C₂H₅ C₂H₅—S—CH₂—CH₂— 189. C₂H₅ C₂H₅—SO₂—CH₂—CH₂— 190. C₂H₅ (CH₃)₂N—CH₂—CH₂— 191. C₂H₅ (C₂H₅)₂N—CH₂—CH₂— 192. C₂H₅ [(CH₃)₂CH]₂N—CH₂—CH₂— 193. C₂H₅ CH₃—O—CH₂—CH(CH₃)— 194. C₂H₅ CH₃S—CH₂—CH(CH₃)— 195. C₂H₅ CH₃—SO₂—CH₂—CH(CH₃)— 196. C₂H₅ C₂H₅—O—CH₂—CH(CH₃)— 197. C₂H_(S) C₂H₅—S—CH₂CH(CH₃)— 198. C₂H₅ C₂H₅—SO₂—CH₂—CH(CH₃)— 199. C₂H₅ (CH₃)₂N—CH₂—CH(CH₃)— 200. C₂H₅ (C₂H₅)₂N—CH₂—CH(CH₃)— 201. C₂H₅ [(CH₃)₂CH]₂N—CH₂—CH(CH₃)— 202. C₂H₅ CH₃—O—CH(CH₃)—CH₂— 203. C₂H₅ CH₃—S—CH(CH₃)—CH₂— 204. C₂H₅ CH₃—SO₂—CH(CH₃)—CH₂— 205. C₂H₅ C₂H₅—O—CH(CH₃)—CH₂— 206. C₂H₅ C₂H₅—S—CH(CH₃)—CH₂— 207. C₂H₅ C₂H₅—SO₂—CH(CH₃)—CH₂— 208. C₂H₅ (CH₃)₂N—CH(CH₃)—CH₂— 209. C₂H₅ (C₂H₅)₂N—CH(CH₃)—CH₂— 210. C₂H_(S) [(CH₃)₂CH]₂N—CH(CH₃)—CH₂— 211. C₂H₅ CH₃—O—CH₂—CH₂—CH₂— 212. C₂H₅ CH₃—S—CH₂—CH₂—CH₂— 213. C₂H₅ CH₃—SO₂—CH₂—CH₂—CH₂— 214. C₂H₅ C₂H₅—O—CH₂—CH₂—CH₂— 215. C₂H₅ C₂H₅—S—CH₂—CH₂—CH₂— 216. C₂H₅ C₂H₅—SO₂—CH₂—CH₂—CH₂— 217. C₂H_(S) (CH₃)₂N—CH₂—CH₂—CH₂— 218. C₂H₅ (C₂H₅)₂N—CH₂—CH₂—CH₂— 219. C₂H₅ CH₃—O—CH₂—C{CH₃)₂— 220. C₂H₅ CH₃—S—CH₂—C(CH₃)₂— 221. C₂H_(S) CH₃—SO₂—CH₂—C(CH₃)₂— 222. C₂H₅ C₂H₅—O—CH₂—C(CH₃)₂— 223. C₂H₅ C₂H₅—S—CH₂—C(CH₃)₂— 224. C₂H₅ C₂H₅—SO₂—CH₂—C(CH₃)₂— 225. C₂H₅ (CH₃)₂N—CH₂—C(CH₃)₂— 226. C₂H₅ (C₂H₅)₂N—CH₂—C(CH₃)₂— 227. C₂H₅ [(CH₃)₂CH]₂N—CH₂—C(CH₃)₂— 228. C₂H₅ Cl—CH₂—C≡C—CH₂— 229. C₂H₅ CH₃—O—C(O)—CH₂ 230. C₂H₅ C₂H₅—O—C(O)—CH₂ 231. C₂H₅ CH₃—O—C(O)—CH(CH₃)— 232. C₂H₅ C₂H₅—O—C(O)—CH{CH₃)— 233. C₂H₅ (CH₃O)₂CH—CH₂— 234. C₂H₅ (C₂H₅O)₂CH—CH₂— 235. OCH₃ H 236. OCH₃ CH₃ 237. OCH₃ CH₃CH₂— 238. OCH₃ (CH₃)₂CH— 239. OCH₃ CH₃CH₂CH₂— 240. OCH₃ n-C₄H₉ 241. OCH₃ (CH₃)₃C— 242. OCH₃ (CH₃)₂CH—CH₂— 243. OCH₃ n-C₅H₁₁ 244. OCH₃ (CH₃)₂CH—CH₂—CH₂— 245. OCH₃ (C₂H₅)₂—CH— 246. OCH₃ (CH₃)₃C—CH₂— 247. OCH₃ (CH₃)₃C—CH₂—CH₂— 248. OCH₃ C₂H₅CH(CH₃)—CH₂— 249. OCH₃ CH₃—CH₂—C(CH₃)₂— 250. OCH₃ (CH₃)₂CH—CH(CH₃)— 251. OCH₃ (CH₃)₃C—CH(CH₃)— 252. OCH₃ (CH₃)₂CH—CH₂—CH(CH₃)— 253. OCH₃ CH₃—CH₂—C(CH₃)(C₂H₅)— 254. OCH₃ CH₃—CH₂—CH₂—C(CH₃)₂— 255. OCH₃ C₂H₅—CH₂—CH(CH₃)—CH₂— 256. OCH₃ cyclopropyl 257. OCH₃ cyclopropyl-CH₂— 258. OCH₃ cyclopropyl-CH(CH₃)— 259. OCH₃ cyclobutyl 260. OCH₃ cyclopentyl 261. OCH₃ cyclohexyl 262. OCH₃ HC≡C—CH₂— 263. OCH₃ HC≡C—CH(CH₃)— 264. OCH₃ HC≡C—C(CH₃)₂— 265. OCH₃ HC≡C—C(CH₃)(C₂H₅)— 266. OCH₃ HC≡C—C(CH₃)(C₃H₇)— 267. OCH₃ CH₂═CH—CH₂— 268. OCH₃ H₂C═CH—CH(CH₃)— 269. OCH₃ H₂C═CH—C(CH₃)₂— 270. OCH₃ H₂C═CH—C(C₂H₅)(CH₃)— 271. OCH₃ C₆H₅—CH₂— 272. OCH₃ 4-(CH₃)₃C—C₆H₄—CH₂— 273. OCH₃ C₆H₅—CH₂— 274. OCH₃ 4-(CH₃)₃C—C₆H₄—CH₂— 275. OCH₃ 4-Cl—C₆H₄—CH₂— 276. OCH₃ 3-(CH₃O)—C₆H₄—CH₂— 277. OCH₃ 4-(CH₃O)—C₆H₄—CH₂— 278. OCH₃ 2-(CH₃O)—C₆H₄—CH₂— 279. OCH₃ 3-CI—C₆H₄—CH₂— 280. OCH₃ 2-Cl—C₆H₄—CH₂— 281. OCH₃ 4-(F₃C)—C₆H₄—CH₂— 282. OCH₃ NC—CH₂— 283. OCH₃ NC—CH₂—CH₂— 284. OCH₃ NC—CH₂—CH(CH₃)— 285. OCH₃ NC—CH₂—C(CH₃)₂— 286. OCH₃ NC—CH₂—CH₂—CH₂— 287. OCH₃ FH₂C—CH₂— 288. OCH₃ ClH₂C—CH₂— 289. OCH₃ BrH₂C—CH₂— 290. OCH₃ FH₂C—CH(CH₃)— 291. OCH₃ ClH₂C—CH(CH₃)— 292. OCH₃ BrH₂C—CH(CH₃)— 293. OCH₃ F₂HC—CH₂— 294. OCH₃ F₃C—CH₂— 295. OCH₃ FH₂C—CH₂—CH₂— 296. OCH₃ ClH₂C—CH₂—CH₂— 297. OCH₃ BrH₂C—CH₂—CH₂— 298. OCH₃ F₂HC—CH₂—CH₂— 299. OCH₃ F₃C—CH₂—CH₂— 300. OCH₃ CH₃—O—CH₂—CH₂— 301. OCH₃ CH₃—S—CH₂—CH₂— 302. OCH₃ CH₃—SO₂—CH₂—CH₂— 303. OCH₃ C₂H₅—O—CH₂—CH₂— 304. OCH₃ (CH₃)₂CH—O—CH₂—CH₂— 305. OCH₃ C₂H₅—S—CH₂—CH₂— 306. OCH₃ C₂H₅SO₂—CH₂—CH₂— 307. OCH₃ (CH₃)₂N—CH₂—CH₂— 308. OCH₃ (C₂H₅)₂N—CH₂—CH₂— 309. OCH₃ [(CH₃)₂CH]₂N—CH_(r)CH₂— 310. OCH₃ CH₃—O—CH₂—CH(CH₃)— 311. OCH₃ CH₃—S—CH₂—CH(CH₃)— 312. OCH₃ CH₃—SO₂—CH₂—CH(CH₃)— 313. OCH₃ C₂H₅—O—CH₂—CH(CH₃)— 314. OCH₃ C₂H₅—S—CH₂—CH(CH₃)— 315. OCH₃ C₂H₅—SO₂—CH₂—CH(CH₃)— 316. OCH₃ (CH₃)₂N—CH₂—CH(CH₃)— 317. OCH₃ (C₂H₅)₂N—CH₂—CH(CH₃)— 318. OCH₃ [(CH₃)₂CH]₂N—CH₂—CH(CH₃)— 319. OCH₃ CH₃—O—CH(CH₃)—CH₂— 320. OCH₃ CH₃—S—CH(CH₃)—CH₂— 321. OCH₃ CH₃—SO₂—CH(CH₃)—CH₂— 322. OCH₃ C₂H₅—O—CH(CH₃)—CH₂— 323. OCH₃ C₂H₅—S—CH{CH₃)—CH₂— 324. OCH₃ C₂H₅—SO₂—CH(CH₃)—CH₂— 325. OCH₃ (CH₃)₂N—CH(CH₃)—CH₂— 326. OCH₃ (C₂H₅)₂N—CH(CH₃)—CH₂— 327. OCH₃ [(CH₃)₂CH]₂N—CH(CH₃)—CH₂— 328. OCH₃ CH₃—O—CH₂—CH₂—CH₂— 329. OCH₃ CH₃—S—CH₂—CH₂—CH₂— 330. OCH₃ CH₃—SO₂—CH₂—CH₂—CH₂— 331. OCH₃ C₂H₅—O—CH₂—CH₂—CH₂— 332. OCH₃ C₂H₅—S—CH₂—CH₂—CH₂— 333. OCH₃ C₂H₅—SO₂—CH₂—CH₂—CH₂— 334. OCH₃ (CH₃)₂N—CH₂—CH₂—CH₂— 335. OCH₃ (C₂H₅)₂N—CH₂—CH₂—CH₂— 336. OCH₃ CH₃—O—CH₂—C(CH₃)₂— 337. OCH₃ CH₃—S—CH₂—C(CH₃)₂— 338. OCH₃ CH₃—SO₂—CH₂—C(CH₃)₂— 339. OCH₃ C₂H₅—O—CH₂—C(CH₃)₂— 340. OCH₃ C₂H₅—S—CH₂—C(CH₃)₂— 341. OCH₃ C₂H₅—SO₂—CH₂—C(CH₃)₂— 342. OCH₃ (CH₃)₂N—CH₂—C(CH₃)₂— 343. OCH₃ (C₂H₅)₂N—CH₂—C(CH₃)₂— 344. OCH₃ [(CH₃)₂CH]₂N—CH₂—C(CH₃)₂— 345. OCH₃ Cl—CH₂—C≡C—CH₂— 346. OCH₃ CH₃—O—C(O)—CH₂— 347. OCH₃ C₂H₅—O—C(O)—CH₂— 348. OCH₃ CH₃—O—C(O)—CH(CH₃)— 349. OCH₃ C₂H₅—O—C(O)—CH(CH₃)— 350. OCH₃ (CH₃O)₂CH—CH₂— 351. OCH₃ (C₂H₅O)₂CH—CH₂— 352. OC₂H₅ H 353. OC₂H₅ CH₃ 354. OC₂H₅ CH₃CH₂— 355. OC₂H₅ (CH₃)₂CH— 356. OC₂H₅ CH₃CH₂CH₂— 357. OC₂H₅ n-C₄H₉ 358. OC₂H₅ (CH₃)₃C— 359. OC₂H₅ (CH₃)₂CH—CH₂— 360. OC₂H₅ n-C₅H₁₁ 361. OC₂H₅ (CH₃)₂CH—CH₂—CH₂— 362. OC₂H₅ (C₂H₅)₂—CH— 363. OC₂H₅ (CH₃)₃C—CH₂— 364. OC₂H₅ (CH₃)₃C—CH₂—CH₂— 365. OC₂H₅ C₂H₅CH(CH₃)—CH₂— 366. OC₂H₅ CH₃—CH₂—C(CH₃)₂— 367. OC₂H₅ (CH₃)₂CH—CH(CH₃)— 368. OC₂H₅ (CH₃)₃C—CH(CH₃)— 369. OC₂H₅ (CH₃)₂CH—CH₂—CH(CH₃)— 370. OC₂H₅ CH₃—CH₂—C(CH₃)(C₂H₅)— 371. OC₂H₅ CH₃—CH₂—CH₂—C(CH₃)₂— 372. OC₂H₅ C₂H₅—CH₂—CH(CH₃)—CH₂— 373. OC₂H₅ cyclopropyl 374. OC₂H₅ cyclopropyl-CH₂— 375. OC₂H₅ cyclopropyl-CH{CH₃)— 376. OC₂H₅ cyclobutyl 377. OC₂H₅ cyclopentyl 378. OC₂H₅ cyclohexyl 379. OC₂H₅ HC≡C—CH₂— 380. OC₂H₅ HC≡C—CH(CH₃)— 381. OC₂H₅ HC≡C—C(CH₃)₂— 382. OC₂H₅ HC≡C—C(CH₃)(C₂H₅)— 383. OC₂H₅ HC≡C—C(CH₃)(C₃H₇)— 384. OC₂H₅ CH₂═CH—CH₂— 385. OC₂H₅ H₂C═CH—CH(CH₃)— 386. OC₂H_(s) H₂C═CH—C(CH₃)₂— 387. OC₂H₅ H₂C═CH—C(C₂H₅)(CH₃)— 388. OC₂H₅ C₆H₅—CH₂— 389. OC₂H₅ 4-(CH₃)₃C—C₆H₄—CH₂— 390. OC₂H₅ C₆H₅—CH₂— 391. OC₂H₅ 4-(CH₃)₃C—C₆H₄—CH₂— 392. OC₂H_(s) 4-Cl—C₆H₄—CH₂— 393. OC₂H₅ 3-(CH₃O)—C₆H₄—CH₂— 394. OC₂H₅ 4-(CH₃O)—C₆H₄—CH₂— 395. OC₂H₅ 2-(CH₃O)—C₆H₄—CH₂— 396. OC₂H_(s) 3-Cl—C₆H₄—CH₂— 397. OC₂H₅ 2-Cl—C₆H₄CH₂— 398. OC₂H₅ 4-(F₃C)—C₆H₄—CH₂— 399. OC₂H₅ NC—CH₂— 400. OC₂H₅ NC—CH₂—CH₂— 401. OC₂H₅ NC—CH₂—CH(CH₃)— 402. OC₂H₅ NC—CH₂—C(CH₃)₂— 403. OC₂H₅ NC—CH₂—CH₂—CH₂— 404. OC₂H₅ FH₂C—CH₂— 405. OC₂H₅ CIH₂C—CH₂— 406. OC₂H₅ BrH₂C—CH₂— 407. OC₂H₅ FH₂C—CH(CH₃)— 408. OC₂H₅ ClH₂C—CH(CH₃)— 409. OC₂H₅ BrH₂C—CH(CH₃)— 410. OC₂H₅ F₂HC—CH₂— 411. OC₂H₅ F₃C—CH₂— 412. OC₂H₅ FH₂C—CH₂—CH₂— 413. OC₂H₅ ClH₂C—CH₂—CH₂— 414. OC₂H₅ BrH₂C—CH₂—CH₂— 415. OC₂H₅ F₂HC—CH₂—CH₂— 416. OC₂H₅ F₃C—CH₂—CH₂— 417. OC₂H₅ CH₃—O—CH₂—CH₂— 418. OC₂H₅ CH₃—S—CH₂—CH₂— 419. OC₂H₅ CH₃—SO₂—CH₂—CH₂— 420. OC₂H_(s) C₂H₅—O—CH₂—CH₂— 421. OC₂H₅ (CH₃)₂CH—O—CH₂—CH₂— 422. OC₂H₅ C₂H₅—S—CH₂—CH₂— 423. OC₂H₅ C₂H₅—SO₂—CH₂—CH₂— 424. OC₂H₅ (CH₃)₂N—CH₂—CH₂— 425. OC₂H₅ (C₂H₅)₂N—CH₂—CH₂— 426. OC₂H₅ [(CH₃)₂CH]₂N—CH₂—CH₂— 427. OC₂H₅ CH₃—O—CH₂—CH(CH₃)— 428. OC₂H₅ CH₃—S—CH₂—CH(CH₃)— 429. OC₂H₅ CH₃—SO₂—CH₂—CH(CH₃)— 430. OC₂H₅ C₂H₅—O—CH₂—CH(CH₃)— 431. OC₂H₅ C₂H₅—S—CH₂—CH(CH₃)— 432. OC₂H₅ C₂H₅—SO₂—CH₂—CH(CH₃)— 433. OC₂H₅ (CH₃)₂N—CH₂—CH(CH₃)— 434. OC₂H₅ (C₂H₅)₂N—CH₂—CH(CH₃)— 435. OC₂H_(s) [(CH₃)₂CH]₂N—CH₂—CH{CH₃)— 436. OC₂H₅ CH₃—O—CH(CH₃)—CH₂— 437. OC₂H₅ CH₃—S—CH(CH₃)—CH₂— 438. OC₂H₅ CH₃—SO₂—CH(CH₃)—CH₂— 439. OC₂H₅ C₂H₅—O—CH(CH₃)—CH₂— 440. OC₂H_(s) C₂H₅—S—CH(CH₃)—CH₂— 441. OC₂H₅ C₂H₅—SO₂—CH(CH₃)—CH₂— 442. OC₂H₅ (CH₃)₂N—CH(CH₃)—CH₂— 443. OC₂H₅ (C₂H₅)₂N—CH(CH₃)—CH₂— 444. OC₂H₅ [(CH₃)₂CH]₂N—CH(CH₃)—CH₂— 445. OC₂H₅ CH₃—O—CH₂—CH₂—CH₂— 446. OC₂H₅ CH₃—S—CH₂—CH₂—CH₂— 447. OC₂H₅ CH₃—SO₂—CH₂—CH₂—CH₂— 448. OC₂H₅ C₂H₅—O—CH₂—CH₂—CH₂— 449. OC₂H₅ C₂H₅—S—CH₂—CH₂—CH₂— 450. OC₂H₅ C₂H₅—SO₂—CH₂—CH₂—CH₂— 451. OC₂H₅ (CH₃)₂N—CH₂—CH₂—CH₂— 452. OC₂H₅ (C₂H₅)₂N—CH₂—CH₂—CH₂— 453. OC₂H_(s) CH₃—O—CH₂—C(CH₃)₂— 454. OC₂H₅ CH₃—S—CH₂—C(CH₃)₂— 455. OC₂H₅ CH₃—SO₂—CH₂—C(CH₃)₂— 456. OC₂H₅ C₂H₅—O—CH₂—C(CH₃)₂— 457. OC₂H₅ C₂H₅—S—CH₂—C(CH₃)₂— 458. OC₂H₅ C₂H₅—SO₂—CH₂—C(CH₃)₂— 459. OC₂H₅ (CH₃)₂N—CH₂—C(CH₃)₂— 460. OC₂H₅ (C₂H₅)₂N—CH₂—C(CH₃)₂— 461. OC₂H_(s) [(CH₃)₂CH]₂N—CH₂—C(CH₃)₂— 462. OC₂H_(S) Cl—CH₂—C≡C—CH₂— 463. OC₂H₅ CH₃—O—C(O)—CH₂— 464. OC₂H₅ C₂H₅—O—C(O)—CH₂— 465. OC₂H₅ CH₃—O—C(O)—CH(CH₃)— 466. OC₂H₅ C₂H₅—O—C(O)—CH(CH₃)— 467. OC₂H₅ (CH₃O)₂CH—CH₂— 468. OC₂H₅ (C₂H₅O)₂CH—CH₂— 469. CF₃ H 470. CF₃ CH₃ 471. CF₃ CH₃CH₂— 472. CF₃ (CH₃)₂CH— 473. CF₃ CH₃CH₂CH₂— 474. CF₃ n-C₄H₉ 475. CF₃ (CH₃)₃C— 476. CF₃ (CH₃)₂CH—CH₂— 477. CF₃ n-C₅H₁₁ 478. CF₃ (CH₃)₂CH—CH₂—CH₂— 479. CF₃ (C₂H₅)₂—CH— 480. CF₃ (CH₃)₃C—CH₂— 481. CF₃ (CH₃)₃C—CH₂—CH₂— 482. CF₃ C₂H₅CH(CH₃)—CH₂— 483. CF₃ CH₃—CH₂—C(CH₃)₂— 484. CF₃ (CH₃)₂CH—CH(CH₃)— 485. CF₃ (CH₃)₃C—CH(CH₃)— 486. CF₃ (CH₃)₂CH—CH₂—CH(CH₃)— 487. CF₃ CH₃—CH₂—C(CH₃)(C₂H₅)— 488. CF₃ CH₃—CH₂—CH₂—C(CH₃)₂— 489.. CF₃ C₂H₅—CH₂—CH(CH₃)—CH₂— 490. CF₃ cyclopropyl 491. CF₃ cyclopropyl-CH₂— 492. CF₃ cyclopropyl-CH{CH₃)— 493. CF₃ cyclobutyl 494. CF₃ cyclopentyl 495. CF₃ cyclohexyl 496. CF₃ HC≡C—CH₂— 497. CF₃ HC≡C—CH(CH₃)— 498. CF₃ HC≡C—C(CH₃)₂— 499. CF₃ HC≡C—C(CH₃)(C₂H₅)— 500. CF₃ HC≡C—C(CH₃)(C₃H₇)— 501. CF₃ CH₂═CH—CH₂— 502. CF₃ H₂C═CH—CH(CH₃)— 503. CF₃ H₂C═CH—C(CH₃)₂— 504. CF₃ H₂C═CH—C(C₂H₅)(CH₃)— 505. CF₃ C₆H₅—CH₂— 506. CF₃ 4-(CH₃)₃C—C₆H₄—CH₂— 507. CF₃ C₆H₅—CH₂— 508. CF₃ 4-(CH₃)₃C—C₆H₄—CH₂— 509. CF₃ 4-Cl—C₆H₄—CH₂— 510. CF₃ 3-(CH₃O)—C₆H₄—CH₂— 511. CF₃ 4-(CH₃O)—C₆H₄—CH₂— 512. CF₃ 2-(CH₃O)—C₆H₄—CH₂— 513. CF₃ 3-Cl—C₆H₄—CH₂— 514. CF₃ 2-Cl—C₆H₄CH₂— 515. CF₃ 4-(F₃C)—C₆H₄—CH₂— 516. CF₃ NC—CH₂— 517. CF₃ NC—CH₂—CH₂— 518. CF₃ NC—CH₂—CH(CH₃)— 519. CF₃ NC—CH₂—C(CH₃)₂— 520. CF₃ NC—CH₂—CH₂—CH₂— 521. CF₃ FH₂C—CH₂— 522. CF₃ ClH₂C—CH₂— 523. CF₃ BrH₂C—CH₂— 524. CF₃ FH₂C—CH(CH₃)— 525. CF₃ ClH₂C—CH(CH₃)— 526. CF₃ BrH₂C—CH(CH₃)— 527. CF₃ F₂HC—CH₂— 528. CF₃ F₃C—CH₂— 529. CF₃ FH₂C—CH₂—CH₂— 530. CF₃ ClH₂C—CH₂—CH₂— 531. CF₃ BrH₂C—CH₂—CH₂— 532. CF₃ F₂HC—CH₂—CH₂— 533. CF₃ F₃C—CH₂—CH₂— 534. CF₃ CH₃—O—CH₂—CH₂— 535. CF₃ CH₃—S—CH₂—CH₂— 536. CF₃ CH₃—SO₂—CH₂—CH₂— 537. CF₃ C₂H₅—O—CH₂—CH₂— 538. CF₃ (CH₃)₂CH—O—CH₂—CH₂— 539. CF₃ C₂H₅—S—CH₂—CH₂— 540. CF₃ C₂H₅—SO₂—CH₂—CH₂— 541. CF₃ (CH₃)₂N—CH₂—CH₂— 542. CF₃ (C₂H₅)₂N—CH₂—CH₂— 543. CF₃ [(CH₃)₂CH]₂N—CH₂—CH₂— 544. CF₃ CH₃—O—CH₂—CH(CH₃)— 545. CF₃ CH₃—S—CH₂—CH(CH₃)— 546. CF₃ CH₃—SO₂—CH₂—CH(CH₃)— 547. CF₃ C₂H₅—O—CH₂—CH(CH₃)— 548. CF₃ C₂H₅—S—CH₂—CH(CH₃)— 549. CF₃ C₂H₅—SO₂—CH₂—CH(CH₃)— 550. CF₃ (CH₃)₂N—CH₂—CH(CH₃)— 551. CF₃ (C₂H₅}₂N—CH₂—CH(CH₃)— 552. CF₃ [(CH₃)₂CH]₂N—CH₂—CH{CH₃)— 553. CF₃ CH₃—O—CH(CH₃)—CH₂— 554. CF₃ CH₃—S—CH(CH₃)—CH₂— 555. CF₃ CH₃—SO₂—CH(CH₃)—CH₂— 556. CF₃ C₂H₅—O—CH(CH₃)—CH₂— 557. CF₃ C₂H₅—S—CH(CH₃)—CH₂— 558. CF₃ C₂H₅—SO₂—CH(CH₃)—CH₂— 559. CF₃ (CH₃)₂N—CH(CH₃)—CH₂— 560. CF₃ (C₂H₅)₂N—CH(CH₃)—CH₂— 561. CF₃ [(CH₃)₂CH]₂N—CH(CH₃)—CH₂— 562. CF₃ CH₃—O—CH₂—CH₂—CH₂— 563. CF₃ CH₃—S—CH₂—CH₂—CH₂— 564. CF₃ CH₃—SO₂—CH₂—CH₂—CH₂— 565. CF₃ C₂H₅—O—CH₂—CH₂—CH₂— 566. CF₃ C₂H₅—S—CH₂—CH₂—CH₂— 567. CF₃ C₂H₅—SO₂—CH₂—CH₂—CH₂— 568. CF₃ (CH₃)₂N—CH₂—CH₂—CH₂— 569. CF₃ (C₂H₅)₂N—CH₂—CH₂—CH₂— 570. CF₃ CH₃—O—CH₂—C(CH₃)₂— 571. CF₃ CH₃—S—CH₂—C(CH₃)₂— 572. CF₃ CH₃—SO₂—CH₂—C(CH₃)₂— 573. CF₃ C₂H₅—O—CH₂—C(CH₃)₂— 574. CF₃ C₂H₅—S—CH₂—C(CH₃)₂— 575. CF₃ C₂H₅—SO₂—CH₂—C(CH₃)₂— 576. CF₃ (CH₃)₂N—CH₂—C(CH₃)₂— 577. CF₃ (C₂H₅)₂N—CH₂—C(CH₃)₂— 578. CF₃ [(CH₃)₂CH]₂N—CH₂—C(CH₃)₂— 579. CF₃ Cl—CH₂—C≡C—CH₂— 580. CF₃ CH₃—O—C(O)—CH₂ 581. CF₃ C₂H₅—O—C(O)—CH₂ 582. CF₃ CH₃—O—C(O)—CH(CH₃)— 583. CF₃ C₂H₅—O—C(O)—CH(CH₃)— 584. CF₃ (CH₃—O)₂CH—CH_(2—) 585. CF₃ (C₂H₅O)₂CH—CH_(2—) 586. OCHF₂ H 587. OCHF₂ CH₃ 588. OCHF₂ CH₃CH₂— 589. OCHF₂ (CH₃)₂CH— 590. OCHF₂ CH₃CH₂CH₂— 591. OCHF₂ n-C₄H₉ 592. OCHF₂ (CH₃)₃C— 593. OCHF₂ (CH₃)₂CH—CH₂— 594. OCHF₂ n-C₅H₁₁ 595. OCHF₂ (CH₃)₂CH—CH₂—CH₂— 596. OCHF₂ (C₂H₅)₂—CH— 597. OCHF₂ (CH₃)₃C—CH₂— 598. OCHF₂ (CH₃)₃C—CH₂—CH₂— 599. OCHF₂ C₂H₅CH(CH₃)—CH₂— 600. OCHF₂ CH₃—CH₂—C(CH₃)₂— 601. OCHF₂ (CH₃)₂CH—CH(CH₃)— 602. OCHF₂ (CH₃)₃C—CH(CH₃)— 603. OCHF₂ (CH₃)₂CH—CH₂—CH(CH₃)— 604. OCHF₂ CH₃CH₂—C(CH₃)(C₂H₅)— 605. OCHF₂ CH₃—CH₂—CH₂—C(CH₃)₂— 606. OCHF₂ C₂H₅—CH₂—CH(CH₃)—CH₂— 607. OCHF₂ cyclopropyl 608. OCHF₂ cyclopropyl-CH₂— 609. OCHF₂ cyclopropyl-CH(CH₃)— 610. OCHF₂ cyclobutyl 611. OCHF₂ cyclopentyl 612. OCHF₂ cyclohexyl 613. OCHF₂ HC≡C—CH₂— 614. OCHF₂ HC≡C—CH(CH₃)— 615. OCHF₂ HC≡C—C(CH₃)₂— 616. OCHF₂ HC≡C—C(CH₃)(C₂H₅)— 617. OCHF₂ HC≡C—C(CH₃)(C₃H₇)— 618. OCHF₂ CH₂═CH—CH₂— 619. OCHF₂ H₂C═CH—CH(CH₃)— 620. OCHF₂ H₂C═CH—C(CH₃)₂— 621. OCHF₂ H₂C═CH—C(C₂H₅)(CH₃)— 622. OCHF₂ C₆H₅—CH₂— 623. OCHF₂ 4-(CH₃)₃C—C₆H₄—CH₂— 624. OCHF₂ C₆H₅—CH₂— 625. OCHF₂ 4-(CH₃)₃C—C₆H₄—CH₂— 626. OCHF₂ 4-Cl—C₆H₄—CH₂— 627. OCHF₂ 3-(CH₃O)—C₆H₄—CH₂— 628. OCHF₂ 4-(CH₃O)—C₆H₄—CH₂— 629. OCHF₂ 2-(CH₃O)—C₆H₄—CH₂— 630. OCHF₂ 3-Cl—C₆H₄—CH₂— 631. OCHF₂ 2-Cl—C₆H₄CH₂— 632. OCHF₂ 4-(F₃C)—C₆H₄—CH₂— 633. OCHF₂ NC—CH₂— 634. OCHF₂ NC—CH₂—CH₂— 635. OCHF₂ NC—CH₂—CH(CH₃)— 636. OCHF₂ NC—CH₂—C(CH₃)₂— 637. OCHF₂ NC—CH₂—CH₂—CH₂— 638. OCHF₂ FH₂C—CH₂— 639. OCHF₂ ClH₂C—CH₂— 640. OCHF₂ BrH₂C—CH₂— 641. OCHF₂ FH₂C—CH(CH₃)— 642. OCHF₂ ClH₂C—CH(CH₃)— 643. OCHF₂ BrH₂C—CH(CH₃)— 644. OCHF₂ F₂HC—CH₂— 645. OCHF₂ F₃C—CH₂— 646. OCHF₂ FH₂C—CH₂—CH₂— 647. OCHF₂ ClH₂C—CH₂—CH₂— 648. OCHF₂ BrH₂C—CH₂—CH₂— 649. OCHF₂ F₂HC—CH₂—CH₂— 650. OCHF₂ F₃C—CH₂—CH₂— 651. OCHF₂ CH₃—O—CH₂—CH₂— 652. OCHF₂ CH₃—S—CH₂—CH₂— 653. OCHF₂ CH₃—SO₂—CH₂—CH₂— 654. OCHF₂ C₂H₅—O—CH₂—CH₂— 655. OCHF₂ (CH₃)₂CH—O—CH₂—CH₂— 656. OCHF₂ C₂H₅—S—CH₂—CH₂— 657. OCHF₂ C₂H₅—SO₂—CH₂—CH₂— 658. OCHF₂ (CH₃)₂N—CH₂—CH₂— 659. OCHF₂ (C₂H₅)₂N—CH₂—CH₂— 660. OCHF₂ [(CH₃)₂CH]₂N—CH₂—CH₂— 661. OCHF₂ CH₃—O—CH₂—CH(CH₃)— 662. OCHF₂ CH₃—S—CH₂—CH(CH₃)— 663. OCHF₂ CH₃—SO₂—CH₂—CH(CH₃)— 664. OCHF₂ C₂H₅—O—CH₂—CH(CH₃)— 665. OCHF₂ C₂H₅—S—CH₂—CH(CH₃)— 666. OCHF₂ C₂H₅—SO₂—CH₂—CH(CH₃)— 667. OCHF₂ (CH₃)₂N—CH₂—CH(CH₃)— 668. OCHF₂ (C₂H₅}₂N—CH₂—CH(CH₃)— 669. OCHF₂ [(CH₃)₂CH]₂N—CH₂—CH{CH₃)— 670. OCHF₂ CH₃—O—CH(CH₃)—CH₂— 671. OCHF₂ CH₃—S—CH(CH₃)—CH₂— 672. OCHF₂ CH₃—SO₂—CH(CH₃)—CH₂— 673. OCHF₂ C₂H₅—O—CH(CH₃)—CH₂— 674. OCHF₂ C₂H₅—S—CH(CH₃)—CH₂— 675. OCHF₂ C₂H₅—SO₂—CH(CH₃)—CH₂— 676. OCHF₂ (CH₃)₂N—CH(CH₃)—CH₂— 677. OCHF₂ (C₂H₅)₂N—CH(CH₃)—CH₂— 678. OCHF₂ [(CH₃)₂CH]₂N—CH(CH₃)—CH₂— 679. OCHF₂ CH₃—O—CH₂—CH₂—CH₂— 680. OCHF₂ CH₃—S—CH₂—CH₂—CH₂— 681. OCHF₂ CH₃—SO₂—CH₂—CH₂—CH₂— 682. OCHF₂ C₂H₅—O—CH₂—CH₂—CH₂— 683- OCHF₂ C₂H₅—S—CH₂—CH₂—CH₂— 684. OCHF₂ C₂H₅—SO₂—CH₂—CH₂—CH₂— 685. OCHF₂ (CH₃)₂N—CH₂—CH₂—CH₂— 686. OCHF₂ (C₂H₅)₂N—CH₂—CH₂—CH₂— 687. OCHF₂ CH₃—O—CH₂—C(CH₃)₂— 688. OCHF₂ CH₃—S—CH₂—C(CH₃)₂— 689. OCHF₂ CH₃—SO₂—CH₂—C(CH₃)₂— 690. OCHF₂ C₂H₅—O—CH₂—C(CH₃)₂— 691. OCHF₂ C₂H₅—S—CH₂—C(CH₃)₂— 692. OCHF₂ C₂H₅—SO₂—CH₂—C(CH₃)₂— 693. OCHF₂ (CH₃)₂N—CH₂—C(CH₃)₂— 694. OCHF₂ (C₂H₅)₂N—CH₂—C(CH₃)₂— 695. OCHF₂ [(CH₃)₂CH]₂N—CH₂—C(CH₃)₂— 696. OCHF₂ Cl—CH₂—C≡C—CH₂— 697. OCHF₂ CH₃—O—C(O)—CH₂ 698. OCHF₂ C₂H₅—O—C(O)—CH₂ 699. OCHF₂ CH₃—O—C(O)—CH(CH₃)— 700. OCHF₂ C₂H₅—O—C(O)—CH(CH₃)— 701. OCHF₂ (CH₃O)₂CH—CH₂— 702. OCHF₂ (C₂H₅O)₂CH—CH₂— 703. OCF₃ H 704. OCF₃ CH₃ 705. OCF₃ CH₃CH₂— 706. OCF₃ (CH₃)₂CH— 707. OCF₃ CH₃CH₂CH₂— 708. OCF₃ n-C₄H₉ 709. OCF₃ (CH₃)₃C— 710. OCF₃ (CH₃)₂CH—CH₂— 711. OCF₃ n-C₅H₁₁ 712. OCF₃ (CH₃)₂CH—CH₂—CH₂— 713. OCF₃ (C₂H₅)₂—CH— 714. OCF₃ (CH₃)₃C—CH₂— 715. OCF₃ (CH₃)₃C—CH₂—CH₂— 716. OCF₃ C₂H₅CH(CH₃)—CH₂— 717. OCF₃ CH₃—CH₂—C(CH₃)₂— 718. OCF₃ (CH₃)₂CH—CH(CH₃)— 719. OCF₃ (CH₃)₃C—CH(CH₃)— 720. OCF₃ (CH₃)₂CH—CH₂—CH(CH₃)— 721. OCF₃ CH₃—CH₂—C(CH₃)(C₂H₅)— 722. OCF₃ CH₃—CH₂—CH₂—C(CH₃)₂— 723, OCF₃ C₂H₅—CH₂—CH(CH₃)—CH₂ ^(—) 724. OCF₃ cyclopropyl 725. OCF₃ cyclopropyl-CH₂— 726. OCF₃ cyclopropyl-CH(CH₃)— 727. OCF₃ cyclobutyl 728. OCF₃ cyclopentyl 729. OCF₃ cyclohexyl 730. OCF₃ HC≡C—CH₂— 731. OCF₃ HC≡C—CH(CH₃)— 732. OCF₃ HC≡C—C(CH₃)₂— 733. OCF₃ HC≡C—C(CH₃)(C₂H₅)— 734. OCF₃ HC≡C—C(CH₃)(C₃H₇)— 735. OCF₃ CH₂═CH—CH₂— 736. OCF₃ H₂C═CH—CH(CH₃)— 737. OCF₃ H₂C═CH—C(CH₃)₂— 738. OCF₃ H₂C═CH—C(C₂H₅)(CH₃)— 739. OCF₃ C₆H₅—CH₂— 740. OCF₃ 4-(CH₃)₃C—C₆H₄—CH₂— 741. OCF₃ C₆H₅—CH₂— 742. OCF₃ 4-(CH₃)₃C—C₆H₄—CH₂— 743. OCF₃ 4-Cl—C₆H₄—CH₂— 744. OCF₃ 3-(CH₃O)—C₆H₄—CH₂— 745. OCF₃ 4-(CH₃O)—C₆H₄—CH₂— 746. OCF₃ 2-(CH₃O)—C₆H₄—CH₂— 747. OCF₃ 3-Cl—C₆H₄—CH₂— 748. OCF₃ 2-Cl—C₆H₄—CH₂— 749. OCF₃ 4-(F₃C)—C₆H₄—CH₂— 750. OCF₃ NC—CH₂— 751. OCF₃ NC—CH₂—CH₂— 752. OCF₃ NC—CH₂—CH(CH₃)— 753. OCF₃ NC—CH₂—C(CH₃)₂— 754. OCF₃ NC—CH₂—CH₂—CH₂— 755. OCF₃ FH₂C—CH₂— 756. OCF₃ ClH₂C—CH₂— 757. OCF₃ BrH₂C—CH₂— 758. OCF₃ FH₂C—CH(CH₃)— 759. OCF₃ ClH₂C—CH(CH₃)— 760. OCF₃ BrH₂C—CH(CH₃)— 761. OCF₃ F₂HC—CH₂— 762. OCF₃ F₃C—CH₂— 763. OCF₃ FH₂C—CH₂—CH₂— 764. OCF₃ ClH₂C—CH₂—CH₂— 765. OCF₃ BrH₂C—CH₂—CH₂— 766. OCF₃ F₂HC—CH₂—CH₂— 767. OCF₃ F₃C—CH₂—CH₂— 768. OCF₃ CH₃—O—CH₂—CH₂— 769. OCF₃ CH₃—S—CH₂—CH₂— 770. OCF₃ CH₃—SO₂—CH₂—CH₂— 771. OCF₃ C₂H₅—O—CH₂—CH₂— 772. OCF₃ (CH₃)₂CH—₀—CH₂—CH₂— 773. OCF₃ C₂H₅—S—CH₂—CH₂— 774. OCF₃ C₂H₅SO₂—CH₂—CH₂— 775. OCF₃ (CH₃)₂N—CH₂—CH₂— 776. OCF₃ (C₂H₅)₂N—CH₂—CH₂— 777. OCF₃ [(CH₃)₂CH]₂N—CH_(r)CH₂— 778. OCF₃ CH₃—O—CH₂—CH(CH₃)— 779. OCF₃ CH₃—S—CH₂—CH(CH₃)— 780. OCF₃ CH₃—SO₂—CH₂—CH(CH₃)— 781. OCF₃ C₂H₅—O—CH₂—CH(CH₃)— 782. OCF₃ C₂H₅—S—CH₂—CH(CH₃)— 783. OCF₃ C₂H₅—SO₂—CH₂—CH(CH₃)— 784. OCF₃ (CH₃)₂N—CH₂—CH(CH₃)— 785. OCF₃ (C₂H₅)₂N—CH₂—CH(CH₃)— 786. OCF₃ [(CH₃)₂CH]₂N—CH₂—CH(CH₃)— 787. OCF₃ CH₃—O—CH(CH₃)—CH₂— 788. OCF₃ CH₃—S—CH(CH₃)—CH₂— 789. OCF₃ CH₃—SO₂—CH(CH₃)—CH₂— 790. OCF₃ C₂H₅—O—CH(CH₃)—CH₂— 791. OCF₃ C₂H₅—S—CH{CH₃)—CH₂— 792. OCF₃ C₂H₅—SO₂—CH(CH₃)—CH₂— 793. OCF₃ (CH₃)₂N—CH(CH₃)—CH₂— 794. OCF₃ (C₂H₅)₂N—CH(CH₃)—CH₂— 795. OCF₃ [(CH₃)₂CH]₂N—CH(CH₃)—CH₂— 796. OCF₃ CH₃—O—CH₂—CH₂—CH₂— 797. OCF₃ CH₃—S—CH₂—CH₂—CH₂— 798. OCF₃ CH₃—SO₂—CH₂—CH₂—CH₂— 799. OCF₃ C₂H₅—O—CH₂—CH₂—CH₂— 800. OCF₃ C₂H₅—S—CH₂—CH₂—CH₂— 801. OCF₃ C₂H₅—SO₂—CH₂—CH₂—CH₂— 802. OCF₃ (CH₃)₂N—CH₂—CH₂—CH₂— 803. OCF₃ (C₂H₅)₂N—CH₂—CH₂—CH₂— 804. OCF₃ CH₃—O—CH₂—C(CH₃)₂— 805. OCF₃ CH₃—S—CH₂—C(CH₃)₂— 806. OCF₃ CH₃—SO₂—CH₂—C(CH₃)₂— 807. OCF₃ C₂H₅—O—CH₂—C(CH₃)₂— 808. OCF₃ C₂H₅—S—CH₂—C(CH₃)₂— 809. OCF₃ C₂H₅—SO₂—CH₂—C(CH)₃)₂— 810. OCF₃ (CH₃)₂N—CH₂—C(CH₃)₂— 811. OCF₃ (C₂H₅)₂N—CH₂—C(CH₃)₂— 812. OCF₃ [(CH₃)₂CH]₂N—CH₂—C(CH₃)₂— 813. OCF₃ Cl—CH₂—C≡C—CH₂— 814. OCF₃ CH₃—O—C(O)—CH₂ 815. OCF₃ C₂H₅—O—C(O)—CH₂ 816. OCF₃ CH₃—O—C(O)—CH(CH₃)— 817. OCF₃ C₂H₅—O—C(O)—CH(CH₃)— 818. OCF₃ (CH₃O)₂CH—CH₂— 819. OCF₃ (C₂H₅O)₂CH—CH₂— 820. OCClF₂ H 821. OCClF₂ CH₃ 822. OCClF₂ CH₃CH₂— 823. OCClF₂ (CH₃)₂CH— 824. OCClF₂ CH₃CH₂CH₂— 825. OCClF₂ n-C₄H₉ 826. OCClF₂ (CH₃)₃C— 827. OCClF₂ (CH₃)₂CH—CH₂— 828. OCClF₂ n-C₅H₁₁ 829. OCClF₂ (CH₃)₂CH—CH₂—CH₂— 830. OCClF₂ (C₂H₅)₂—CH— 831. OCClF₂ (CH₃)₃C—CH₂— 832. OCClF₂ (CH₃)₃C—CH₂—CH₂— 833. OCClF₂ C₂H₅CH(CH₃)—CH₂— 834. OCClF₂ CH₃—CH₂—C(CH₃)₂— 835. OCClF₂ (CH₃)₂CH—CH(CH₃)— 836. OCClF₂ (CH₃)₃C—CH(CH₃)— 837. OCClF₂ (CH₃)₂CH—CH₂—CH(CH₃)— 838. OCClF₂ CH₃CH₂—C(CH₃)(C₂H₅)— 839. OCClF₂ CH₃—CH₂—CH₂—C(CH₃)₂— 840. OCClF₂ C₂H₅—CH₂—CH(CH₃)—CH₂— 841. OCClF₂ cyclopropyl 842. OCClF₂ cyclopropyl-CH₂— 843. OCClF₂ cyclopropyl-CH(CH₃)— 844. OCClF₂ cyclobutyl 845. OCClF₂ cyclopentyl 846. OCClF₂ cyclohexyl 847. OCClF₂ HC≡C—CH₂— 848. OCClF₂ HC≡C—CH(CH₃)— 849. OCClF₂ HC≡C—C(CH₃)₂— 850. OCClF₂ HC≡C—C(CH₃)(C₂H₅)— 851. OCClF₂ HC≡C—C(CH₃)(C₃H₇)— 852. OCClF₂ CH₂—CH—CH₂— 853. OCClF₂ H₂C═CH—CH(CH₃)— 854. OCClF₂ H₂C═CH—C(CH₃)₂— 855. OCClF₂ H₂C═CH—C(C₂H₅)(CH₃)— 856. OCClF₂ C₆H₅—CH₂— 857. OCClF₂ 4-(CH₃)₃C—C₆H₄—CH₂— 858. OCClF₂ C₆H₅—CH₂— 859. OCClF₂ 4-(CH₃)₃C—C₆H₄—CH₂— 860. OCClF₂ 4-Cl—C₆H₄—CH₂— 861. OCClF₂ 3-(CH₃O)—C₆H₄—CH₂— 862. OCClF₂ 4-(CH₃O)—C₆H₄—CH₂— 863. OCClF₂ 2-(CH₃O)—C₆H₄—CH₂— 864. OCClF₂ 3-Cl—C₆H₄—CH₂— 865. OCClF₂ 2-Cl—C₆H₄—CH₂— 866. OCClF₂ 4-(F₃C)—C₆H₄—CH₂— 867. OCClF₂ NC—CH₂— 868. OCClF₂ NC—CH₂—CH₂— 869. OCClF₂ NC—CH₂—CH(CH₃)— 870. OCClF₂ NC—CH₂—C(CH₃)₂— 871. OCClF₂ NC—CH₂—CH₂—CH₂— 872. OCClF₂ FH₂C—CH₂— 873. OCClF₂ ClH₂C—CH₂— 874. OCClF₂ BrH₂C—CH₂— 875. OCClF₂ FH₂C—CH(CH₃)— 876. OCClF₂ ClH₂C—CH(CH₃)— 877. OCClF₂ BrH₂C—CH(CH₃)— 878. OCClF₂ F₂HC—CH₂— 879. OCClF₂ F₃C—CH₂— 880. OCClF₂ FH₂C—CH₂—CH₂— 881. OCClF₂ ClH₂C—CH₂—CH₂— 882. OCClF₂ BrH₂C—CH₂—CH₂— 883. OCClF₂ F₂HC—CH₂—CH₂— 884. OCClF₂ F₃C—CH₂—CH₂— 885. OCClF₂ CH₃—O—CH₂—CH₂— 886. OCClF₂ CH₃—S—CH₂—CH₂— 887. OCClF₂ CH₃—SO₂—CH₂—CH₂— 888. OCClF₂ C₂H₅—O—CH₂—CH₂— 889. OCClF₂ (CH₃)₂CH—O—CH₂—CH₂— 890. OCClF₂ C₂H₅—S—CH₂—CH₂— 891. OCClF₂ C₂H₅SO₂—CH₂—CH₂— 892. OCClF₂ (CH₃)₂N—CH₂—CH₂— 893. OCClF₂ (C₂H₅)₂N—CH₂—CH₂— 894. OCClF₂ [(CH₃)₂CH]₂N—CH_(r)CH₂— 895. OCClF₂ CH₃—O—CH₂—CH(CH₃)— 896. OCClF₂ CH₃—S—CH₂—CH(CH₃)— 897. OCClF₂ CH₃—SO₂—CH₂—CH(CH₃)— 898. OCClF₂ C₂H₅—O—CH₂—CH(CH₃)— 899. OCClF₂ C₂H₅—S—CH₂—CH(CH₃)— 900. OCClF₂ C₂H₅—SO₂—CH₂—CH(CH₃)— 901. OCClF₂ (CH₃)₂N—CH₂—CH(CH₃)— 902. OCClF₂ (C₂H₅)₂N—CH₂—CH(CH₃)— 903. OCClF₂ [(CH₃)₂CH]₂N—CH₂—CH(CH₃)— 904. OCClF₂ CH₃—O—CH(CH₃)—CH₂— 905. OCClF₂ CH₃—S—CH(CH₃)—CH₂— 906. OCClF₂ CH₃—SO₂—CH(CH₃)—CH₂— 907. OCClF₂ C₂H₅—O—CH(CH₃)—CH₂— 908. OCClF₂ C₂H₅—S—CH(CH₃)—CH₂— 909. OCClF₂ C₂H₅—SO₂—CH(CH₃)—CH₂— 910. OCClF₂ (CH₃)—N—CH(CH₃)—CH₂— 911. OCClF₂ (C₂H₅)₂—N—CH(CH₃)—CH₂— 912. OCClF₂ [(CH₃)₂CH]₂N—CH(CH₃)—CH₂— 913. OCClF₂ CH₃—O—CH₂—CH₂—CH₂— 914. OCClF₂ CH₃—S—CH₂—CH₂—CH₂— 915. OCClF₂ CH₃—SO₂—CH₂—CH₂—CH₂— 916. OCClF₂ C₂H₅—O—CH₂—CH₂—CH₂— 917. OCClF₂ C₂H₅—S—CH₂—CH₂—CH₂— 918. OCClF₂ C₂H₅—SO₂—CH₂—CH₂—CH₂— 919. OCClF₂ (CH₃)₂N—CH₂—CH₂—CH₂— 920. OCClF₂ (C₂H₅)₂N—CH₂—CH₂—CH₂— 921. OCClF₂ CH₃—O—CH₂—C(CH₃)₂— 922. OCClF₂ CH₃—S—CH₂—C(CH₃)₂— 923. OCClF₂ CH₃—SO₂—CH₂—C(CH₃)₂— 924. OCClF₂ C₂H₅—O—CH₂—C(CH₃)₂— 925. OCClF₂ C₂H₅—S—CH₂—C(CH₃)₂— 926. OCClF₂ C₂H₅—SO₂—CH₂—C(CH₃)₂— 927. OCClF₂ (CH₃)₂N—CH₂—C(CH₃)₂— 928. OCClF₂ (C₂H₅)₂N—CH₂—C(CH₃)₂— 929. OCClF₂ [(CH₃)₂CH]₂N—CH₂—C(CH₃)₂— 930. OCClF₂ Cl—CH₂—C≡C—CH₂— 931. OCClF₂ CH₃—O—C(O)—CH₂ 932. OCClF₂ C₂H₅—O—C(O)—CH₂ 933. OCClF₂ CH₃—O—C(O)—CH(CH₃)— 934. OCClF₂ C₂H₅—O—C(O)—CH(CH₃)— 935. OCClF₂ (CH₃O)₂CH—CH₂— 936. OCClF₂ (C₂H₅O)₂CH—CH₂—

The following compounds of the formula (I), which can optionally be present in their isomeric formulae (I-A) and (I-B), are explicitly known from the publications cited at the start,

wherein R¹, R², R³, R⁵ have the meaning stated in table B and R⁴ and A mean hydrogen.

TABLE B Example No. R³ R⁵ R¹ R² M.Pt. [° C.] 1 H H CH₃ n-CH₂CH₂CH₃ 74-77 2 H H OCH₃ —CH₃ 121-128 3 Cl H CH₃ —CH₂CH₃ 85-90 4 CN CH₃ CH₃ —CH₃ 178-180 5 Br H CH₃ —CH₂CH₃ 112-114 6 Br H CH₃ cyclopropyl 140-142 7 Br H CH₃ n-C₄H₉ 112-116 8 Br H CH₃ —CH(CH₃)₂ 102-103 9 Br H CH₃ n-CH₂CH₂CH₃ 119-120 10 Br H CH₃ C₆H₅—CH₂— 139-140 11 Br H CH₃ 4-(CH₃)₃C—C₆H₄—CH₂— 147-151 12 H H CH₃ C₆H₅—CH₂— 117-119 13 H H CH₃ 4-(CH₃)₃C—C₆H₄—CH₂—  97-103 14 H H CH₃ 4-Cl—C₆H₄—CH₂— 150-151 15 Br H CH₃ 3-(CH₃O)—C₆H₄—CH₂— 123-125 16 H H CH₃ 3-(CH₃O)—C₆H₄—CH₂— 117-122 17 Br H CH₃ 4-(CH₃O)—C₆H₄—CH₂— 156-161 18 H H CH₃ 4-(CH₃O)—C₆H₄—CH₂— 127-132 19 Br H CH₃ 2-(CH₃O)—C₆H₄—CH₂— 103-108 20 H H CH₃ 2-(CH₃O)—C₆H₄—CH₂— 127-130 21 Br H CH₃ 4-Cl—C₆H₄—CH₂— 127-131 22 Br H CH₃ 3-Cl—C₆H₄—CH₂— 102-108 23 H H CH₃ 3-Cl—C₆H₄—CH₂— 118-125 24 Br H CH₃ 2-Cl—C₆H₄—CH₂— 118-125 25 H H CH₃ 2-Cl—C₆H₄—CH₂— 128-131 26 Br H CH₃ 4-(F₃C)—C₆H₄—CH₂— 153-155 27 H H CH₃ 4-(F₃C)—C₆H₄—CH₂— 135-137 28 Br H CH₃ cyclopropyl-CH₂— 106-110 29 H H CH₃ —CH₃ 83-89 30 H H CH₃ —CH₂CH₃  98-103 31 H H CH₃ prop-2-ynyl 104-107 32 Br H CH₃ —CH₂—CN 106-110 33 H H CH₃ cyclopropyl-CH₂— 89-93 34 H H CH₃ —CH₂—CN 130-134 35 Br H CH₃ prop-2-ynyl ¹H-NMR 36 Br H CH₃ (CH₃)₃C—CH₂— 112-114 37 H H CH₃ (CH₃)₃C—CH₂— 86-93 38 H H CH₃ CH₂═CHCH₂— ¹H-NMR 39 H H OCH₃ —CH₂CH₃ 121-126 40 H H OCH₃ C₆H₅—CH₂— 108-119 41 H H OCH₃ —CH(CH₃)₂ 104-113 42 H H OCH₃ prop-2-ynyl 122-138 43 H H OCH₃ —CH₂—CN ¹H-NMR 44 H H OCH₃ CH₂═CHCH₂— ¹H-NMR 45 H H OCH₃ H 186-198 46 Cl H CH₃ —CH₃ 112-122 47 Cl H CH₃ H 160-162 48 H H OCH₂CH₃ —CH₃ 91-95 49 H H OCH₂CH₃ —CH₂CH₃ 111-113 50 H H OCH₂CH₃ H 183-186 51 CI H CH₃ C₆H₅—CH₂— 132-135 52 Cl H CH₃ —CH(CH₃)₂ 86-94 53 Cl H CH₃ prop-2-ynyl ¹H-NMR 54 Cl H CH₃ H₂C═CHCH₂— 95-96 55 Cl H CH₃ FH₂CCH₂— 115-121 56 H H OCH₂CH₃ C₆H₅—CH₂— oil 57 H H OCH₂CH₃ prop-2-ynyl 105-112 58 H H OCH₂CH₃ —CH₂—CN 129-134 59 H H OCH₂H₃ CH₂═CHCH₂— oil 60 H H OCH₂CH₃ —CH₂—CH₂—CH₃ 113-115 61 H H OCH₂CH₃ cyclopropyl-CH₂ 128-130 62 Cl H CH₃ —CH₂—CN 134-138 63 H H OCH₂CH₃ —CH₂—CF₃ oil 64 H H OCH₂CH═CH₂ —CH₂—CH₃ oil 65 H H OCH(CH₃)₂ —CH₂—CH₃ oil 66 H H OCHF₂ —CH₂—CH₃  98-100 67 H H OCH(CH₃)₂ H 132-136 68 H H OCH(CH₃)₂ prop-2-ynyl oil 69 H H OCH(CH₃)₂ —CH₂CN oil 70 H H OCH(CH₃)₂ cyclopropyl oil 71 H H OCH(CH₃)₂ —CH(CH₃)₂ oil 72 H H OCH(CH₃)₂ C₆H₅—CH₂— oil 73 H H OCH(CH₃)₂ —CH₂—CH₃ oil 74 Br H CH₃ H 149-151 75 H H CH₃ H 171-174 76 H H OCH(CH₃)₂ O—CH₂—CH₃ oil 77 H H OCH(CH₃)₂ —CH₂—CH₂—CH₃ oil 78 H H OCHF₂ H 135-137 79 H H OCHF₂ —CH₂—C≡CH 65-70 80 H H OCH₂CHClCH₂Cl H 123-129 81 H H OCH(CH₃)₂ —CH₃ 82-91 82 H H OCH₃ —CH₂-c-C₃H₅ 92-95 83 H H OCH₃ -c-C₃H₅ 142-148 84 H H OCH₃ —O—CH₂CH₃ 138-143 85 H H OCH₃ —CH₂—CH₂—CN 123-130 86 H H OCH₃ —CH₂—CH₂—S—CH₃ oil 87 H H OCH₃ —CH₂—CH₂—S(O)₂—CH₃ 157-160 88 H H OCH₃ —CH₂—CH₂F 134-140 89 H H OCHF₂ H 122-128 90 H H OCH₃ —CH₂—CF₃ 136-141 91 H H OCH₃ —CH₂—CHF₂ 116-118 92 H H OCH₃ —O—CH₃ 136-139 93 Br H OCH₃ —CH₂—C≡CH 110-115 94 H H OCH₃ —CH₂—CH₂—N(CH₃)₂ 94-97 95 Br H OCH₃ —CH₂—C₆H₅ 134-136 96 H H OCHF₂ —CH₂—CF₃ 120-138 97 H H OCHF₂ —CH₂—C₆H₅ 115-117 98 H H OCHF₂ -c-C₃H₅ 87-91 99 H H OCHF₂ —CH₂—CH₂—S—CH₃ ¹H-NMR 100 Br H OCHF₂ —CH₃ 168-173 101 H H OCHF₂ —CH₂—CH═CH₂ 75-78 102 H H OCHF₂ —CH₂-c-C₃H₅ ¹H-NMR 103 H H OCHF₂ —CH₂—CH₂—CH₃ 54-58 104 H H OCHF₂ —CH₂—CH₂—O—CH₃ ¹H-NMR 105 H H OCHF₂ —CH₂—CH₂—CN 83-88 106 H H OCHF₂ —CH—(CH₃)₂ 72-74 107 H H OCHF₂ —CH₂—CHF₂ 92-96 108 H H OCHF₂ —O—CH₃ oil 109 H H CF₃ —CH₂—CH₃ 81-86 110 H H CF₃ —CH₂—C≡CH 106-111 111 H H CF₃ —CH₂—C₆H₅ 106-108 112 H H CF₃ —CH₃ 104-113 113 H H CF₃ —CH₂—CH═CH₂ 71-73 114 H H CF₃ —CH—(CH₃)₂ 65-67 115 H H CF₃ —CH₂—CH₂—CH₃ 62-66 116 H H CF₃ —CH₂-c-C₃H₅ oil 117 H H CF₃ —CH₂—CF₃ oil 118 H H CF₃ —CH₂—CH₂—S—CH₃ oil 119 H H CF₃ -c-C₃H₅ 94-96 120 H H CF₃ —O—CH₂—CH₃ 118-120 121 H H CF₃ —CH₂—CH₂—SO₂—CH₃ 169-171 122 H H CH₃ —O—CH₂—CH₃ 118-121 123 H H CH₃ —O—CH₃ 136-140 124 H H CH₃ cyclobutyl HPLC/MS 125 H H CH₃ cyclopentyl HPLC/MS 126 H H CH₃ cyclohexyl HPLC/MS 127 H H CH₃ cyclopropyl HPLC/MS 128 H H CH₃ —C(CH₃)₂—CH₂—CH₃ HPLC/MS 129 H H CH₃ —CH₂—CH₂—CH₂—N(C₂H₅)₂ HPLC/MS 130 H H CH₃ —CH(CH₃)—CH(CH₃)₂ HPLC/MS 131 H H CH₃ —CH(CH₃)—C(CH₃)₃ HPLC/MS 132 H H CH₃ —C(CH₃)₃ HPLC/MS 133 H H CH₃ —C(CH₃)(C₂H₅)—CH₂—CH₃ HPLC/MS 134 H H CH₃ —C(CH₃)₂—CH₂—CH₂—CH₃ HPLC/MS 135 H H CH₃ —CH₂—CH₂—N[CH(CH₃)₂]₂ HPLC/MS 136 H H CH₃ —CH₂—CH₂—O—C₂H₅ HPLC/MS 137 H H CH₃ —CH(C₂H₅)₂ HPLC/MS 138 H H CH₃ —CH(CH₃)—CH₂—CH(CH₃)₂ HPLC/MS 139 H H CH₃ —CH(C₂H₅)—CH₂—O—CH₃ HPLC/MS 140 H H CH₃ —C(CH₃)₂—C≡CH HPLC/MS 141 H H CH₃ —CH(CH₃)—CH₂—O—C₂H₅ HPLC/MS 142 H H CH₃ CH(CH₃)—CH₂—O—CH₃ HPLC/MS 143 H H CH₃ —CH₂—CH(CH₃)—C₂H₅ HPLC/MS 144 H H CH₃ —CH(CH₃)—CH₂—S—CH₃ HPLC/MS 145 H H CH₃ —CH₂—CH(OCH₃)₂ ¹H-NMR 146 H H CH₃ —CH₂—CH₂—C(CH₃)₃ HPLC/MS 147 H H CH₃ —CH₂—CH(OC₂H₅)₂ HPLC/MS 148 H H CH₃ —CH₂—CH₂—S—CH₃ HPLC/MS 149 H H CH₃ —CH₂—CH(CH₃)₂ HPLC/MS 150 H H CH₃ —CH₂—CH₂—CH(CH₃)₂ HPLC/MS 151 H H CH₃ —CH₂—CH₂—CH₂—O—CH₃ HPLC/MS 152 H H CH₃ —CH₂—CH(CH₃)—O—CH₃ HPLC/MS 153 H H CH₃ —CH₂—CH(CH₃)—CH₂C₂H₅ HPLC/MS 154 H H CH₃ —CH₂—CH₂—CH₂—S—CH₃ HPLC/MS 155 H H CH₃ —C(CH₃)₂—CH₂—S—C₂H₅ HPLC/MS 156 H H CH₃ —C(CH₃)₂—CH₂—S—CH₃ HPLC/MS 157 H H CH₃ —CH(CH₃)—CH₂—N(CH₃)₂ HPLC/MS 158 H H CH₃ —C(CH₃)(n-C₃H₇)₂—C≡CH HPLC/MS 159 H H CH₃ —C(CH₃)₂—CH═CH₂ HPLC/MS 160 H H CH₃ —CH(CH₃)—C(O)—O—CH₃ HPLC/MS 161 H H CH₃ —CH(CH₃)-c-C₃H₅ HPLC/MS 162 H H CH₃ —CH₂—CF₃ HPLC/MS 163 H H CH₃ —CH₂—CH₂—O—CH₃ HPLC/MS 164 H H CH₃ —CH(CH₃)—C₂H₅ HPLC/MS 165 H H CH₃ CH(CH₃)₂ HPLC/MS 166 H H CH₃ —C(CH₃)₂—CH₂—CN HPLC/MS 167 H H CH₃ —CH₂—CH₂—CH₂—N(CH₃)₂ HPLC/MS 168 H H CH₃ —CH₂—CH₂—CH₂—CH₂—CH₃ HPLC/MS 169 H H CH₃ —CH₂—CH₂—F HPLC/MS 170 H H CH₃ —CH₂—CH₂—CH₂—O—C₂H₅ HPLC/MS 171 H H CH₃ —CH₂—CH₂—O—CH(CH₃)₂ HPLC/MS 172 H H CH₃ —CH(CH₃)—CH₂—Cl HPLC/MS 173 H H CH₃ CH₂—CH₂—CH₂—Cl HPLC/MS 174 H H CH₃ —CH₂—C≡C—CH₂—Cl HPLC/MS 175 H H CH₃ —CH₂—C(O)—O—CH₃ HPLC/MS 176 H H CH₃ —CH₂—CH₂—CH₂—Br HPLC/MS 177 H H CH₃ —CH₂—CH₂—CH₂—CH₃ HPLC/MS 178 H H CH₃ —CH₂—CH₂—S—C₂H₅ HPLC/MS 179 CN H CH₃ —CH₂—CH₃ 114-119 180 CN H CH₃ —CH₃ 172-175 181 CN H CH₃ —CH₂—C≡CH  95-105 182 CN H CH₃ H oil 183 CN H CH₃ —CH₂—CH═CH₂ 83-95 184 CN H CH₃ —CH₂—CH₂—CH₃ 95-99 185 CN H CH₃ —CH₂—CH₂—F oil 186 CN H CH₃ cyclopropyl oil 187 CN H CH₃ —O—CH₃ 139-142 188 OCH₃ H CH₃ —CH₂—CH₃ 171-174 189 OCH₃ H CH₃ —CH₂—C≡CH 151-155 190 OCH₃ H CH₃ —H 171-180 191 OCH₃ H CH₃ —CH₃ 171-175 192 H Cl CH₃ CH₂CH₃ 119-123 193 H Br CH₃ CH₂CH₃ 141-144 Here M.Pt. means melting point c-C₃H₅: cyclopropyl, and n-C₃H₇: n-propyl

Furthermore, the following compounds of the formula (I) are explicitly known from the publications cited at the start,

where A, R¹, R², R³, R⁵ have the meaning stated in table C and R⁴ means hydrogen.

TABLE C Example No. A R² R¹ R³ R⁵ M.Pt. [° C.] 194 C₂H₅ C₂H₅ OCH₃ H H 77-83 195 CH₂CH═CH₂ CH₂CH═CH₂ OCH₃ H H 60-73 196 CH₃ CH₃ OCH₃ Br H 75-80 197 CH₃ CH₃ OCH₃ H NO₂ oil 198 CH₃ C₂H₅ OCHF₂ H H oil 199 CH₃ CH₃ OCH₃ H NH₂ oil 200 C₂H₅ C₂H₅ OCHF₂ H H oil 201 CH₃ CH₃ OC₂H₅ H H 86-94 202 C₂H₅ C₂H₅ OC₂H₅ H H oil 203 CH₃ CH₃ OCH(CH₃)₂ H H oil 204 CH₃ CH₃ OCH₂CHClCH₂Cl H H oil 205 CH₃ CH₃ OCF₂—Cl H H 83-85 206 CH₃ CH₃ OCF₃ H H 95-98 207 CH₃ C₂H₅ OCF₃ H H oil 208 C₂H₅ C₂H₅ OCF₃ H H oil 209 CH₃ C₂H₅ OCF₂Cl H H oil 210 C₂H₅ C₂H₅ OCF₂Cl H H oil 211 CH₃ CH₃ OCH₃ H CH₃ 89-93 212 CH₃ GH₃ OCH₃ H C₂H₅ 138-140 213 CH₃ CH₃ OCH₃ H CH₃OCO 134-138 214 CH₃ CH₃ OCH₃ H Cl LC/MS 215 CH₃ CH₃ OCH₃ H H ¹H-NMR 216 CH₃ C₂H₅ OCF₂—CHFCl H H ¹H-NMR 217 CH₃ CH₃ OCH₃ H F 123-125 218 CH₃ C₂H₅ OCH₃ H F ¹H-NMR 219 CH₃ CH(CH₃)₂ OCH₃ H F ¹H-NMR 220 CH₃ CH₂C≡CH OCH₃ H F ¹H-NMR 221 CH₃ CH₃ OCH₃ OCH₃ H ¹H-NMR 222 CH₃ CH₃ OCHF₂ H F 102-105 223 CH₃ CH₃ OCH₃ Cl Br 93-98 224 CH₃ CH₃ OCH₃ F H ¹H-NMR 225 CH₃ CH₂—CH═CH₂ OCH₃ H H Here, M.Pt. = melting point.

Some of the compounds set out in table B and C are characterized by ¹H NMR or by LC-MS. The results are set out in WO 2005/035486 and WO 2006/056433. Reference is hereby expressly made to the content of these publications.

Further, the following compound of the formula (I-226) and isomeric forms thereof 1-226-A and 1-226-B are explicitly known from the publications cited at the start,

Examples 225 and 42-A are characterized by ¹H NMR. The signals are defined by a chemical shift (in ppm) relative to tetramethylsilane, by their multiplicity and their integral, the number of hydrogen atoms corresponding thereto being stated in the brackets in each case. Here m means multiplet, t triplet, d doublet and s singlet. The results are set out below:

Ex. 225:

¹H-NMR (400 mHz, d₆-DMSO: δ=2.77 ppm (s, 3H, NCH₃); 3.82-3.81 ppm (d, 2H, N—CH₂); 4.00 ppm (s, 3H, OCH₃); 5.19-5.27 ppm (m, 2H, CH═CH₂); 5.68-5.78 ppm (m, 1H, CH═CH₂); 7.56-7.58 ppm (2H, CH); 7.83-7.87 ppm (1H, CH).

Ex. 42-A:

¹H-NMR (400 mHz, d₆-DMSO: δ=9.20 ppm (1H, ═NH); 7.91-7.88 (1H, CH); 7.73-7.71 ppm (1H, CH); 7.61-7.60 (1H, CH); 4.52 ppm (2H, N—CH₂); 4.07 ppm (3H, O—CH₃); 3.28 ppm (t, 1H, C≡CH).

EXAMPLE A Activity Increase Due to Ammonium Salts

Myzus persicae-Test (MYZUPE)

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

For the preparation of a suitable active substance preparation, 1 part by weight of active substance is mixed with the stated quantities of solvent and emulsifier and the concentrate is diluted to the desired concentration with emulsifier-containing water. When addition of ammonium salts is necessary, these are in each case pipetted into the finished preparation solution in a concentration of 1000 ppm after dilution.

Paprika plants (Capsicum annuum) which are severely infested by the green peach aphid (Myzus persicae) are treated by spraying with the active substance preparation in the desired concentration.

After the desired time, the kill rate in % is determined. Here 100% means that all the animals were killed; 0% means that no animals were killed.

TABLE A Active substance Kill rate/% after 6 days Active substance ppm a.i. +AS (1000 ppm) 42 20 5 20 42-A 20 0 45 45-B*  4 35  60 AS = ammonium sulfate *known from EP 33984, Ex. 33

EXAMPLE B Activity Increase Due to Ammonium Salts

Aphis gossypii-Test (APHIGO)

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

For the preparation of a suitable active substance preparation, 1 part by weight of active substance is mixed with the stated quantities of solvent and emulsifier and the concentrate is diluted to the desired concentration with emulsifier-containing water. When addition of ammonium salts is necessary, these are in each case pipetted into the finished preparation solution in a concentration of 1000 ppm after dilution.

Cotton leaves (Gossypium hirsutum) which are severely infested with the cotton aphid (Aphis gossypii) are sprayed with an active substance preparation with the desired concentration.

After the desired time, the kill rate in % is determined. Here 100% means that all the aphids were killed; 0% means that no aphids were killed.

TABLE B Active Kill rate/ substance % after 6 days Active substance ppm a.i. +AS (1000 ppm) 42-A 20 30 98 42-A 4 15 55  44 4 5 25 225 20 35 75 AS = ammonium sulfate

EXAMPLE C Activity Increase Due to Ammonium Salts in Combination with Penetration Enhancers

Myzus persicae—Test (MYZUPE)

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 (table C1)/1 (table C2) parts by weight of alkylaryl polyglycol ether

For the preparation of a suitable active substance preparation, 1 part by weight of active substance is mixed with the stated quantities of solvent and emulsifier and the concentrate is diluted to the desired concentration with emulsifier-containing water. When addition of ammonium salts, penetration enhancers or ammonium salts and penetration enhancers is necessary, these are in each case pipetted into the finished preparation solution in a concentration of 1000 ppm after dilution.

Paprika plants (Capsicum annuum) which are severely infested with the green peach aphid (Myzus persicae) are treated by spraying with the active substance preparation in the desired concentration.

After the desired time, the kill rate in % is determined. Here 100% means that all the animals were killed; 0% means that no animals were killed.

TABLE C1 Kill rate/% after 6 days Active +RME + Active substance +AS +RME AS (each substance ppm a.i. (1000 ppm) (1000 ppm) 1000 ppm)  42 100 75 80 99 100  42 20 5 20 25 70  42-A 20 0 45 90 98 226 20 10 10 25 50  44 20 85 70 85 98  44 4 10 15 20 30 225 4 0 0 5 35 RME = rape oil methyl ester (formulated as 500 EW, concentration stated in g active substance/1) AS = ammonium sulfate

TABLE C2 Kill rate/% after 7 days Active +RME + Active substance +AS +RME AS (each substance g/ha a.i. (1000 ppm) (1000 ppm) 1000 ppm) 83 60 0 0 10 75 215 60 0 20 40 75 40 60 0 0 40 50 AS = ammonium sulfate RME = rape oil methyl ester

EXAMPLE D Activity Increase Due to Ammonium Salts in Combination with Penetration Enhancers

Aphis gossypii-Test (APHIGO)

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 (table D1)/1 (table D2) parts by weight of alkylaryl polyglycol ether

For the preparation of a suitable active substance preparation, 1 part by weight of active substance is mixed with the stated quantities of solvent and emulsifier and the concentrate is diluted to the desired concentration with emulsifier-containing water. When addition of ammonium salts, penetration enhancers or ammonium salts and penetration enhancers is necessary, these are in each case pipetted into the finished preparation solution in a concentration of 1000 ppm after dilution.

Cotton leaves (Gossypium hirsutum) which are severely infested with the cotton aphid (Aphis gossypii) are sprayed with an active substance preparation with the desired concentration.

After the desired time, the kill rate in % is determined. Here 100% means that all the aphids were killed; 0% means that no aphids were killed.

TABLE D1 Kill rate/% after 6 days Active +RME + Active substance +AS +RME AS (each substance ppm a.i. (1000 ppm) (1000 ppm) 1000 ppm) 226 4 20 20 35 55 226 0.8 0 0 20 35 44 4 5 25 45 55 RME = rape oil methyl ester (formulated as 500 EW, concentration stated in g active substance/1) AS = ammonium sulfate

TABLE D2 Kill rate/% after 7 days Active +RME + Active substance +RME +AS AS (each substance g/ha a.i. (1000 ppm) (1000 ppm) 1000 ppm) 83 2.4 10 30 55 85 41 2.4 50 10 80 93 AS = ammonium sulfate RME = rape oil methyl ester

EXAMPLE E Activity Increase Due to Ammonium Salts Tetranychus-Test (OP-Resistant)

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

For the preparation of a suitable active substance preparation, 1 part by weight of active substance is mixed with the stated quantities of solvent and emulsifier and the concentrate is diluted to the desired concentration with emulsifier-containing water. When addition of ammonium salts is necessary, these are in each case pipetted into the finished preparation solution in a concentration of 1000 ppm after dilution.

Bean plants (Phaseolus vulgaris) which are severely infested by all stages of the common spider mite (Tetranychus urticae) are treated by spraying with the active substance preparation in the desired concentration.

After the desired time, the kill rate in % is determined. here 100% means that all the spider mites were killed; 0% means that no spider mites were killed.

TABLE E Active Kill rate/ substance % after 6 days Active substance ppm a.i. +AS (1000 ppm) 44 20 40 70 225 20 20 80 AS = ammonium sulfate

EXAMPLE F Activity Increase Due to Ammonium Salts in Combination with Penetration Enhancers Tetranychus-Test (OP-Resistant)

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

For the preparation of a suitable active substance preparation, 1 part by weight of active substance is mixed with the stated quantities of solvent and emulsifier and the concentrate is diluted to the desired concentration with emulsifier-containing water. When addition of ammonium salts, penetration enhancers or ammonium salts and penetration enhancers is necessary, these are in each case pipetted into the finished preparation solution in a concentration of 1000 ppm after dilution.

Bean plants (Phaseolus vulgaris) which are severely infested by all stages of the common spider mite (Tetranychus urticae) are treated by spraying with the active substance preparation in the desired concentration.

After the desired time, the kill rate in % is determined. here 100% means that all the spider mites were killed; 0% means that no spider mites were killed.

TABLE F Kill rate/% after 6 days Active +RME + Active substance +AS +RME AS (each substance ppm a.i. (1000 ppm) (1000 ppm) 1000 ppm)  42-A 4 70 50 75 95  42-A 0.8 50 30 45 80 226 20 50 70 60 90 RME = rape oil methyl ester (formulated as 500 EW, concentration stated in g active substance/1) AS = ammonium sulfate 

1. A composition comprising at least one insecticidal and/or acaricidal active substance of the 2-cyanobenzene-sulfonamide class and isomeric forms thereof at least one salt of the formula (II)

in which D stands for nitrogen or phosphorus, R⁶, R⁷, R⁸ and R⁹ mutually independently stand for hydrogen or each for optionally substituted C₁-C₈ alkyl or singly or multiply unsaturated, optionally substituted C₁-C₈ alkylene, wherein the substituents can be selected from halogen, nitro and cyano, n stands for 1, 2, 3 or 4, and R¹⁰ stands for an inorganic or organic anion.
 2. The composition as claimed in claim 1, characterized in that the active substance is a 2-cyanobenzenesulfonamide of the general formula (I)

in which A stands for hydrogen, C₁-C₆ alkyl or C₂-C₆ alkenyl R¹ stands for hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy or C₁-C₄ haloalkoxy; R² stands for hydrogen, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl or C₁-C₄ alkoxy, where the five last-named residues can be unsubstituted, partly or completely halogenated and/or can bear one, two or three residues from the group C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C_(a) haloalkoxy, C₁-C₄ haloalkylthio, C₁-C₄ alkoxycarbonyl, cyano, amino, (C₁-C₄ alkyl)amino, di-(C₁-C₄ alkyl)amino, C₃-C₈ cycloalkyl and phenyl, wherein the phenyl can be unsubstituted, partly or completely halogenated and/or can bear one, two or three substituents from the group C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy and C₁-C₄ haloalkoxy; and R³, R⁴ and R⁵ mutually independently stand for hydrogen, halogen, cyano, nitro, C₁-C₆ alkyl, C₃-C₈ cycloalkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C_(a) alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkoxy, C₁-C₄ haloalkylthio, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₄ alkoxycarbonyl, amino, (C₁-C₄ alkyl)amino, di-(C₁-C₄ alkyl)amino, aminocarbonyl, (C₁-C₄ alkyl)aminocarbonyl and di-(C₁-C₄ alkyl)aminocarbonyl.
 3. The composition as claimed in claim 1 or 2, characterized in that the active substance is a 2-cyanobenzenesulfonamide of the general formula (I) and/or the isomeric form (I-A)

in which R¹ stands for hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C_(a) alkoxy or C₁-C₄ haloalkoxy; R² stands for C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₈ cycloalkyl or C₁-C₄ alkoxy, where the five last-named residues can be unsubstituted, partly or completely halogenated and/or can bear one, two or three residues from the group C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkoxy, C₁-C₄ haloalkylthio, C₁-C₄ alkoxycarbonyl, cyano, amino, (C₁-C₄ alkyl)amino, di-(C₁-C₄ alkyl)amino, C₃-C₈ cycloalkyl and phenyl, wherein the phenyl can be unsubstituted, partly or completely halogenated and/or can bear one, two or three substituents from the group C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C_(a) alkoxy and C₁-C₄ haloalkoxy; and R³, R⁴ and R⁵ mutually independently stand for hydrogen, halogen, cyano, nitro, C₁-C₆ alkyl, C₃-C₈ cycloalkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkoxy, C₁-C₄ haloalkylthio, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₄ alkoxycarbonyl, amino, (C₁-C₄ alkyl)amino, di-(C₁-C₄ alkyl)amino, aminocarbonyl, (C₁-C₄ alkyl)aminocarbonyl and di-(C₁-C₄ alkyl)aminocarbonyl.
 4. The composition as claimed in claim 1 or 2, characterized in that the active substance is a 2-cyanobenzenesulfonamide of the general formula (I) and/or the isomeric form (I-B)

in which R¹, R³, R⁴, R⁵ have the meanings stated in claim
 2. 5. The composition as claimed in claims 1 to 4, characterized in that the active substance content is between 0.5 and 50 wt. %.
 6. The composition as claimed in claims 1 to 5, characterized in that the content of ammonium or phosphonium salt is between 0.5 and 80 mmol/l.
 7. The composition as claimed in claims 1 to 6, characterized in that D stands for nitrogen.
 8. The composition as claimed in claim 7, characterized in that R¹⁰ stands for hydrogen carbonate, tetraborate, fluoride, bromide, iodide, chloride, monohydrogen phosphate, dihydrogen phosphate, hydrogen sulfate, tartrate, sulfate, nitrate, thiosulfate, thiocyanate, formate, lactate, acetate, propionate, butyrate, pentanoate, citrate or oxalate.
 9. The composition as claimed in claim 7, characterized in that R¹⁰ stands for thiocyanate, dihydrogen phosphate, monohydrogen phosphate or sulfate.
 10. The composition as claimed in claim 7, characterized in that R¹⁰ stands for sulfate.
 11. The composition as claimed in claims 1 to 10, characterized in that it contains at least one penetration enhancer.
 12. The composition as claimed in claim 11, characterized in that the penetration enhancer is a fatty alcohol alkoxylate of the formula (III) R—O-(-AO)_(v—)R′  (III) in which R stands for linear or branched alkyl with 4 to 20 carbon atoms, R′ stands for hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl or n-hexyl, AO stands for an ethylene oxide residue, a propylene oxide residue, a butylene oxide residue or for mixtures of ethylene oxide and propylene oxide residues or butylene oxide residues and v stands for numbers from 2 to 30, or a mineral or vegetable oil or the ester of a mineral or vegetable oil.
 13. The composition as claimed in claim 11, characterized in that the penetration enhancer is rape oil methyl ester.
 14. The composition as claimed in claims 1 to 13, characterized in that the content of penetration enhancer is 1 to 95 wt. %.
 15. A method for the control of noxious insects and/or spider mites, characterized in that a composition as claimed in one or more of claims 1 to 14 is applied undiluted or diluted onto insects and/or spider mites or their habitat in such quantity that an effective quantity of the insecticidal active substances contained acts on the insects and/or spider mites or their habitat.
 16. A method for increasing the action of pesticides containing an active substance from the 2-cyanobenzenesulfonamide class of the general formula (I) and/or isomeric forms thereof (I-A) or (I-B) as claimed in claims 2 to 4, characterized in that the ready-to-use agent (spray) is prepared with the use of a salt of the formula (II) as claimed in claim
 1. 17. The method as claimed in claim 16, characterized in that the spray is prepared with the use of a penetration enhancer.
 18. The method as claimed in claim 16 or 17, characterized in that the penetration enhancer is present in a final concentration of 0.1 to 10 g/l and/or the salt of the formula (II) is present in a final concentration of 0.5 to 80 mmol/l.
 19. Use of a salt of the formula (II) as claimed in claim 1 for increasing the action of a pesticide containing an active substance of the 2-cyanobenzenesulfonamide class of the general formula (I) and/or an isomeric form (I-A) or (I-B) thereof as claimed in claims 2 to 4, characterized in that the salt is used in the preparation of a ready-to-use pesticide (spray).
 20. The use according to claim 19, characterized in that the salt of the formula (II) is present in the ready-to-use pesticide in a concentration of 0.5 to 80 mmol/l.
 21. The use according to claim 19 or 20, characterized in that the salt is used in the preparation of a ready-to-use pesticide (spray), which also contains a penetration enhancer. 